L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]- → HCID 131715024, compound

HRID 236466Notes

Reaction equation

HRID 236466 reaction equation
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:20][CH2:21][C:22]([NH:24][C@H:25]([C:27]([O:29][CH3:30])=[O:28])[CH3:26])=[O:23].Cl>>[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([NH:20][CH2:21][C:22]([NH:24][C@H:25]([C:27]([O:29][CH3:30])=[O:28])[CH3:26])=[O:23])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 71777655HCID 71777655, compound

Product 1

HCID 131715024HCID 131715024, compoundYield 74.1%

Procedure

Boc-Phe-OH (26.5 g, 100 mmol) was coupled to H-Gly-Ala-OCH3.HCl (19.6 g, 100 mmol) using a mixed anhydride procedure. After crystallization from ethyl acetate:hexane, 30.2 g of Boc-Phe-Gly-Ala-OCH3 (m.p. 126.4°-127.8°) were obtained.

Workup

  1. customAfter crystallization from ethyl acetate

Sources & evidence

ORD record
ord-511824506561431f879a79710940f900
Source dataset
uspto-grants-1987_02
Patent number
US04644055

Reaction notes

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