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【结 构 式】

【分子编号】27105

【品名】benzyl (2S)-1-((2S)-2-[[(2S)-2-[[(2S)-2-amino-4-methylpentanoyl]amino]-4-(benzyloxy)-4-oxobutanoyl]amino]-3-methylbutanoyl)-2-pyrrolidinecarboxylate

【CA登记号】

【 分 子 式 】C34H46N4O7

【 分 子 量 】622.762

【元素组成】C 65.57% H 7.45% N 9% O 17.98%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(X)

N-Boc-L-Valine N-hydroxysuccinimidyl ester (I) was coupled to L-proline benzyl ester (II), and the resulting Boc dipeptide (III) was subsequently deprotected with trifluoroacetic acid in CH2Cl2 to afford (IV). This was condensed with N-Boc-L-aspartic acid gamma-benzyl 1-N-hydroxysuccinimidyl diester (V) to give (VI). After Boc deprotection of (VI) with trifluoroacetic acid, tripeptide (VII) was coupled with N-Boc-L-leucine N-hydroxysuccinimidyl ester (VIII) to yield tetrapeptide (IX). Further Boc deprotection of (IX) with trifluoroacetic acid furnished peptide intermediate (X).

1 Ateeq, H.S.; Lin, K.-C.; Hsiung, S.H.; et al.; Selective, tight-binding inhibitors of integrin alpha4beta1 that inhibit allergic airway responses. J Med Chem 1999, 42, 5, 920.
2 Lin, K.-C.; Adams, S.P.; Castro, A.C.; Zimmerman, C.N.; Cuervo, J.H.; Lee, W.-C.; Hammond, C.E.; Carter, M.B.; Almquist, R.G.; Ensinger, C.L. (Biogen, Inc.); Cell adhesion inhibitor. EP 0842196; JP 1999511124; WO 9703094 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 27097 tert-butyl (1S)-1-[[(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)oxy]carbonyl]-2-methylpropylcarbamate C14H20N2O6 详情 详情
(II) 20930 benzyl (2S)-2-pyrrolidinecarboxylate 16652-71-4 C12H15NO2 详情 详情
(III) 27098 benzyl (2S)-1-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-methylbutanoyl]-2-pyrrolidinecarboxylate C22H32N2O5 详情 详情
(IV) 27099 benzyl (2S)-1-[(2S)-2-amino-3-methylbutanoyl]-2-pyrrolidinecarboxylate C17H24N2O3 详情 详情
(V) 27100 benzyl (3S)-3-[(tert-butoxycarbonyl)amino]-4-[(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)oxy]-4-oxobutanoate C20H22N2O8 详情 详情
(VI) 27101 benzyl (2S)-1-[(2S)-2-([(2S)-4-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]-4-oxobutanoyl]amino)-3-methylbutanoyl]-2-pyrrolidinecarboxylate C33H43N3O8 详情 详情
(VII) 27102 benzyl (2S)-1-((2S)-2-[[(2S)-2-amino-4-(benzyloxy)-4-oxobutanoyl]amino]-3-methylbutanoyl)-2-pyrrolidinecarboxylate C28H35N3O6 详情 详情
(VIII) 27103 tert-butyl (1S)-1-[[(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)oxy]carbonyl]-3-methylbutylcarbamate C15H22N2O6 详情 详情
(IX) 27104 benzyl (2S)-1-[(2S,5S,8S)-5-[2-(benzyloxy)-2-oxoethyl]-8-isobutyl-2-isopropyl-12,12-dimethyl-4,7,10-trioxo-11-oxa-3,6,9-triazatridec-1-anoyl]-2-pyrrolidinecarboxylate C39H54N4O9 详情 详情
(X) 27105 benzyl (2S)-1-((2S)-2-[[(2S)-2-[[(2S)-2-amino-4-methylpentanoyl]amino]-4-(benzyloxy)-4-oxobutanoyl]amino]-3-methylbutanoyl)-2-pyrrolidinecarboxylate C34H46N4O7 详情 详情

合成路线2

该中间体在本合成路线中的序号:(X)

Condensation of o-tolyl isocyanate (XI) with 4-aminophenylacetic acid (XII) produced urea (XIII). This was coupled to tetrapeptide (X) using EDC and HOBt to give the corresponding amide (XIV). Finally, the benzyl ester groups of (XIV) were deprotected by hydrogenolysis over Pd/C.

1 Ateeq, H.S.; Lin, K.-C.; Hsiung, S.H.; et al.; Selective, tight-binding inhibitors of integrin alpha4beta1 that inhibit allergic airway responses. J Med Chem 1999, 42, 5, 920.
2 Lin, K.-C.; Adams, S.P.; Castro, A.C.; Zimmerman, C.N.; Cuervo, J.H.; Lee, W.-C.; Hammond, C.E.; Carter, M.B.; Almquist, R.G.; Ensinger, C.L. (Biogen, Inc.); Cell adhesion inhibitor. EP 0842196; JP 1999511124; WO 9703094 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(X) 27105 benzyl (2S)-1-((2S)-2-[[(2S)-2-[[(2S)-2-amino-4-methylpentanoyl]amino]-4-(benzyloxy)-4-oxobutanoyl]amino]-3-methylbutanoyl)-2-pyrrolidinecarboxylate C34H46N4O7 详情 详情
(XI) 27106 1-isocyanato-2-methylbenzene 614-68-6 C8H7NO 详情 详情
(XII) 21229 2-(4-Aminophenyl)acetic acid 5345-54-0 C8H9NO2 详情 详情
(XIII) 27107 2-[4-[(2-toluidinocarbonyl)amino]phenyl]acetic acid C16H16N2O3 详情 详情
(XIV) 27108 benzyl (2S)-1-((2S)-2-[[(2S)-4-(benzyloxy)-2-([(2S)-4-methyl-2-[(2-[4-[(2-toluidinocarbonyl)amino]phenyl]acetyl)amino]pentanoyl]amino)-4-oxobutanoyl]amino]-3-methylbutanoyl)-2-pyrrolidinecarboxylate C50H60N6O9 详情 详情
Extended Information