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

HRID 1110697Notes

Reaction equation

HRID 1110697 reaction equation
[NH:1]([C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])[CH2:2][C:3]([NH:5][C@H:6]([C:14]([NH:16][CH2:17][C:18]([NH:20][C@H:21]([C:25]([NH:27][CH2:28][C:29]([NH:31][C@H:32]([C:34]([NH:36][CH2:37][C:38]([NH:40][C@H:41]([C:45]([N:47]1[CH2:61][CH2:60][CH2:59][C@H:48]1[C:49]([O:51]CC1C=CC=CC=1)=[O:50])=[O:46])[CH:42]([CH3:44])[CH3:43])=[O:39])=[O:35])[CH3:33])=[O:30])=[O:26])[CH:22]([CH3:24])[CH3:23])=[O:19])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].N(C(OC(C)(C)C)=O)[C@H](C(NCC(O)=O)=O)C>>[NH:1]([C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])[CH2:2][C:3]([NH:5][C@H:6]([C:14]([NH:16][CH2:17][C:18]([NH:20][C@H:21]([C:25]([NH:27][CH2:28][C:29]([NH:31][C@H:32]([C:34]([NH:36][CH2:37][C:38]([NH:40][C@H:41]([C:45]([N:47]1[CH2:61][CH2:60][CH2:59][C@H:48]1[C:49]([OH:51])=[O:50])=[O:46])[CH:42]([CH3:44])[CH3:43])=[O:39])=[O:35])[CH3:33])=[O:30])=[O:26])[CH:22]([CH3:24])[CH3:23])=[O:19])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]

Participants

3

Reactant 2

HCID 192414(S)-2-(2-((tert-Butoxycarbonyl)amino)propanamido)acetic acidHCID 131715253Boc-Gly-Phe-Gly-Val-Gly-Ala-Gly-Val-Pro-OBzl

Product 1

HCID 131715256Boc-Gly-Phe-Gly-Val-Gly-Ala-Gly-Val-Pro-OH

Procedure

The above peptide XV was hydrogenated as described for the preparation VIII to obtain the product in quantitative yield. Rf3 0.22. Anal. calcd. for C40H61N9O12:C 55.66, H 7.12, N 14.60%. Found: C 55.86, H 7.23, N 14.14%.

Workup

  1. customto obtain the product in quantitative yield

Sources & evidence

ORD record
ord-30dc1d449a2247ffb4e2b521972541e5
Source dataset
uspto-grants-1990_12
Patent number
US04976734

Reaction notes

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