2-[((2S)-2-[[(benzyloxy)carbonyl]amino]-4-methylpentanoyl)amino]acetic acid -Drug Synthesis Database

【结构式】

【分子编号】46318

【品名】2-[((2S)-2-[[(benzyloxy)carbonyl]amino]-4-methylpentanoyl)amino]acetic acid

【CA登记号】

【分子式】C₁₆H₂₂N₂O₅

【分子量】322.36116

【元素组成】C 59.62% H 6.88% N 8.69% O 24.82%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(VI)

Condensation of the Weinreb amide of N-Boc-proline (I) with the lithium anion of benzothiazole (II) in THF at -78 C gave benzothiazolyl ketone (III), which was reduced with NaBH4 to afford the diastereomeric mixture of alcohols (IV). Deprotection of the Boc group of (IV) by means of HCl in EtOAc provided pyrrolidine (V). This was then coupled with Z-leucyl-glycine (VI) in the presence of PyBOP to give the peptidyl alcohol (VII). Finally, Swern oxidation of (VII) furnished the corresponding ketone.

参考文献中间体

合成目标

【1】 Santana, J.; Gullet, C.; Schrével, J.; Frappier, F.; Maoulida, C.; Grellier, P.; Joyeau, R.; Teixeira, A.R.L.; Synthesis and activity of pyrrolidinyl- and thiazolidinyl-dipeptide derivatives as inhibitors of the Tc80 prolyl oligopeptidase from Trypanosoma cruzi. Eur J Med Chem 2000, 35, 2, 257.

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)	46320	tert-butyl (2S)-2-[[methoxy(methyl)amino]carbonyl]-1-pyrrolidinecarboxylate		C₁₂H₂₂N₂O₄	详情	详情
(II)	36784	1,3-benzothiazole	95-16-9	C₇H₅NS	详情	详情
(III)	46321	tert-butyl (2S)-2-(1,3-benzothiazol-2-ylcarbonyl)-1-pyrrolidinecarboxylate		C₁₇H₂₀N₂O₃S	详情	详情
(IV)	46322	tert-butyl (2S)-2-[(R)-1,3-benzothiazol-2-yl(hydroxy)methyl]-1-pyrrolidinecarboxylate		C₁₇H₂₂N₂O₃S	详情	详情
(V)	46323	(R)-1,3-benzothiazol-2-yl[(2S)pyrrolidinyl]methanol		C₁₂H₁₄N₂OS	详情	详情
(VI)	46318	2-[((2S)-2-[[(benzyloxy)carbonyl]amino]-4-methylpentanoyl)amino]acetic acid		C₁₆H₂₂N₂O₅	详情	详情
(VII)	46324	benzyl (1S)-1-[[(2-[(2S)-2-[(R)-1,3-benzothiazol-2-yl(hydroxy)methyl]pyrrolidinyl]-2-oxoethyl)amino]carbonyl]-3-methylbutylcarbamate		C₂₈H₃₄N₄O₅S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

Prolinamide (I) was coupled with Z-leucylglycine (II) in the presence of DCC and HOBt to give the tripeptide amide (III). The terminal carboxamido group of (III) was then dehydrated to the corresponding nitrile by treatment with SOCl2 and N-methylmorpholine.

参考文献中间体

合成目标

【1】 Santana, J.; Gullet, C.; Schrével, J.; Frappier, F.; Maoulida, C.; Grellier, P.; Joyeau, R.; Teixeira, A.R.L.; Synthesis and activity of pyrrolidinyl- and thiazolidinyl-dipeptide derivatives as inhibitors of the Tc80 prolyl oligopeptidase from Trypanosoma cruzi. Eur J Med Chem 2000, 35, 2, 257.

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)	36137	(2S)-2-pyrrolidinecarboxamide;L-prolinamide	7531-52-4	C₅H₁₀N₂O	详情	详情
(II)	46318	2-[((2S)-2-[[(benzyloxy)carbonyl]amino]-4-methylpentanoyl)amino]acetic acid		C₁₆H₂₂N₂O₅	详情	详情
(III)	46319	benzyl (1S)-1-[([2-[(2S)-2-(aminocarbonyl)pyrrolidinyl]-2-oxoethyl]amino)carbonyl]-3-methylbutylcarbamate		C₂₁H₃₀N₄O₅	详情	详情

Extended Information