N-(tert-butoxycarbonyl)glycine → Boc-Gly-Phe-Gly-Val-Gly-OBzl

HRID 2309172Notes

Reaction equation

HRID 2309172 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:10]([NH:12][CH2:13][C:14]([NH:16][C@H:17]([C:21]([NH:23][CH2:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])=[O:22])[CH:18]([CH3:20])[CH3:19])=[O:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH:42]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:43][C:44]([OH:46])=O>>[NH:42]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:43][C:44]([NH:1][C@H:2]([C:10]([NH:12][CH2:13][C:14]([NH:16][C@H:17]([C:21]([NH:23][CH2:24][C:25]([O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26])=[O:22])[CH:18]([CH3:20])[CH3:19])=[O:15])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)=[O:46]

Participants

3

Reactant 2

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 131715249Boc-Phe-Gly-Val-Gly-OBzl2×

Product 1

HCID 131715248Boc-Gly-Phe-Gly-Val-Gly-OBzlYield 98.6%

Procedure

III (8.0 g, 14 mmol) was deblocked as described for II and coupled with Boc-Gly-OH by the excess mixed anhydride method and worked up as described under III to obtain the title compound in 98.6% yield, Rf2 0.75. Anal. Calcd. for C32H43N5O8 : C 61.42, H 6.92, N 11.19%. Found: C 61.12, H 7.21, N 11.19%.

Sources & evidence

ORD record
ord-f915d52009e34e9aa9e9719396150174
Source dataset
uspto-grants-1987_09
Patent number
US04693718

Reaction notes

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