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

HRID 1110692Notes

Reaction equation

HRID 1110692 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.NCC(N[C@H](C(NCC(OCC1C=CC=CC=1)=O)=O)C(C)C)=O.[NH:65]([C:70]([O:72][C:73]([CH3:76])([CH3:75])[CH3:74])=[O:71])[CH2:66][C:67]([OH:69])=O>>[NH:65]([C:70]([O:72][C:73]([CH3:76])([CH3:75])[CH3:74])=[O:71])[CH2:66][C:67]([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:69]

Participants

4

Reactant 3

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 131715249Boc-Phe-Gly-Val-Gly-OBzl2×HCID 131716728H-Gly-Val-Gly-OBzl

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-11996bb4645b498cb13395ed09aa9a5d
Source dataset
uspto-grants-1990_12
Patent number
US04976734

Reaction notes

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