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【结 构 式】

【分子编号】40872

【品名】tert-butyl (1S)-2-[[(1S)-2-amino-1-benzyl-2-oxoethyl]amino]-1-benzyl-2-oxoethylcarbamate

【CA登记号】

【 分 子 式 】C23H29N3O4

【 分 子 量 】411.50108

【元素组成】C 67.13% H 7.1% N 10.21% O 15.55%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(III)

The condensation of resin bounded L-phenylalanine (I) with N-(tert-butoxycarbonyl)-L-phenylalanine (II) by means of 1,3-diisopropylcarbodiimide (DIC) and HOBT gives the protected, resin bounded dipeptide (III), which is deprotected with TFA to yield the dipeptide (IV). The reductocondensation of (IV) with 2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carbaldehyde (V) by means of NaBH3CN affords the protected pseudo tripeptide (VI), which is deprotected with TFA as before yielding the pseudo tripeptide (VII). The condensation of (VII) with the protected L-dimethyltyrosine (VIII) by means of DIC and HOBT affords the protected resin bounded seudotetrapeptide (IX), which is deprotected with TFA as before giving the resin bounded seudotetrapeptide (X). Finally, the target seudotetrapeptide is cleaved from the resin by means of HF and anisole.

1 Chung, N.N.; Weltrowska, G.; Fundytus, M.E.; Merovitz, L.; Schiller, P.W.; Coderre, T.J.; Nguyen, T.M.D.; Lemieux, C.; The opioid mu agonist/delta antagonist DIPP-NH2[psi] produces a potent analgesic effect, no physical dependence, and less tolerance than morphine in rats. J Med Chem 1999, 42, 18, 3520.
2 Schiller, P. (AstraZeneca plc); New peptides. EP 0678099; JP 1996505386; WO 9415959 .
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) 19032 (2S)-2-amino-3-phenylpropanamide 5241-58-7 C9H12N2O 详情 详情
(II) 12874 (2R)-2-[(tert-Butoxycarbonyl)amino]-3-phenylpropionic acid; N-alpha-t-BOC-L-Phenylalanine 13734-34-4 C14H19NO4 详情 详情
(III) 40872 tert-butyl (1S)-2-[[(1S)-2-amino-1-benzyl-2-oxoethyl]amino]-1-benzyl-2-oxoethylcarbamate C23H29N3O4 详情 详情
(IV) 19034 (2S)-2-amino-N-[(1S)-2-amino-1-benzyl-2-oxoethyl]-3-phenylpropanamide C18H21N3O2 详情 详情
(V) 40873 tert-butyl 3-formyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate C15H19NO3 详情 详情
(VI) 40874 tert-butyl 3-[[((1S)-2-[[(1S)-2-amino-1-benzyl-2-oxoethyl]amino]-1-benzyl-2-oxoethyl)amino]methyl]-3,4-dihydro-2(1H)-isoquinolinecarboxylate C33H40N4O4 详情 详情
(VII) 40875 (2S)-3-phenyl-2-([(2S)-3-phenyl-2-[(1,2,3,4-tetrahydro-3-isoquinolinylmethyl)amino]propanoyl]amino)propanamide C28H32N4O2 详情 详情
(VIII) 40876 (2S)-2-[(tert-butoxycarbonyl)amino]-3-[4-[(tert-butoxycarbonyl)oxy]-2,6-dimethylphenyl]propionic acid C21H31NO7 详情 详情
(IX) 40877 4-[(2S)-3-[3-[[((1S)-2-[[(1S)-2-amino-1-benzyl-2-oxoethyl]amino]-1-benzyl-2-oxoethyl)amino]methyl]-3,4-dihydro-2(1H)-isoquinolinyl]-2-[(tert-butoxycarbonyl)amino]-3-oxopropyl]-3,5-dimethylphenyl tert-butyl carbonate C49H61N5O8 详情 详情
(X) 40878 (2S)-N-[(1S)-2-amino-1-benzyl-2-oxoethyl]-2-[([2-[(2S)-2-amino-3-(4-hydroxy-2,6-dimethylphenyl)propanoyl]-1,2,3,4-tetrahydro-3-isoquinolinyl]methyl)amino]-3-phenylpropanamide C39H45N5O4 详情 详情
Extended Information