(S)-2-(2-((tert-Butoxycarbonyl)amino)propanamido)acetic acid → Boc-Ala-Gly-Val-Pro-Gly-Phe-Gly-Val-Gly-OH

HRID 1110694Notes

Reaction equation

HRID 1110694 reaction equation
[NH:1]([C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])[C@H:2]([C:4]([NH:6][CH2:7][C:8]([NH:10][C@H:11]([C:15]([N:17]1[CH2:61][CH2:60][CH2:59][C@H:18]1[C:19]([NH:21][CH2:22][C:23]([NH:25][C@H:26]([C:34]([NH:36][CH2:37][C:38]([NH:40][C@H:41]([C:45]([NH:47][CH2:48][C:49]([O:51]CC1C=CC=CC=1)=[O:50])=[O:46])[CH:42]([CH3:44])[CH3:43])=[O:39])=[O:35])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:24])=[O:20])=[O:16])[CH:12]([CH3:14])[CH3:13])=[O:9])=[O:5])[CH3:3].N(C(OC(C)(C)C)=O)[C@H](C(NCC(O)=O)=O)C>O>[NH:1]([C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])[C@H:2]([C:4]([NH:6][CH2:7][C:8]([NH:10][C@H:11]([C:15]([N:17]1[CH2:61][CH2:60][CH2:59][C@H:18]1[C:19]([NH:21][CH2:22][C:23]([NH:25][C@H:26]([C:34]([NH:36][CH2:37][C:38]([NH:40][C@H:41]([C:45]([NH:47][CH2:48][C:49]([OH:51])=[O:50])=[O:46])[CH:42]([CH3:43])[CH3:44])=[O:39])=[O:35])[CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:24])=[O:20])=[O:16])[CH:12]([CH3:13])[CH3:14])=[O:9])=[O:5])[CH3:3]

Participants

4

Reactant 2

HCID 192414(S)-2-(2-((tert-Butoxycarbonyl)amino)propanamido)acetic acidHCID 131715251Boc-Ala-Gly-Val-Pro-Gly-Phe-Gly-Val-Gly-OBzl

Product 1

HCID 131715250Boc-Ala-Gly-Val-Pro-Gly-Phe-Gly-Val-Gly-OH

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The nonapeptide benzylester (IX) was hydrogenated as described under VIII to obtain the acid in quantitative yield. Rf3 0 24. Anal. calcd. for C40H61N9O12 .H2O: C 55.09, H 7.16, N 14.3%. Found: C 54.69, H 7.16, N 13.81%.

Workup

  1. customto obtain the acid in quantitative yield

Sources & evidence

ORD record
ord-11a1cca102d3474abec61f6d41418d27
Source dataset
uspto-grants-1990_12
Patent number
US04976734

Reaction notes

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