Tert-butoxycarbonylalanine → Boc-AlaAlaPro-OBzl

HRID 615339Notes

Reaction equation

HRID 615339 reaction equation
[NH:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:2]([C:4]([OH:6])=O)[CH3:3].[NH2:14][C@H:15]([C:17]([N:19]1[CH2:33][CH2:32][CH2:31][C@H:20]1[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])=[O:18])[CH3:16].Cl.N(C(OC(C)(C)C)=O)[C@H](C(N1CCC[C@H]1C(OCC1C=CC=CC=1)=O)=O)C>>[NH:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:2]([C:4]([NH:14][C@H:15]([C:17]([N:19]1[CH2:33][CH2:32][CH2:31][C@H:20]1[C:21]([O:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:22])=[O:18])[CH3:16])=[O:6])[CH3:3]

Participants

4

Reactant 3

HCID 85082Tert-butoxycarbonylalanineHCID 13034412L-alanyl-L-proline, phenylmethyl ester, hydrochlorideHCID 13068139N-[(1,1-Dimethylethoxy)carbonyl]-L-alanyl-L-proline phenylmethyl ester

Product 1

HCID 15289361Boc-AlaAlaPro-OBzlYield 36.5%

Procedure

Boc-Ala-OH (11.5 g, 48.4 mmoles) was coupled to H-AlaPro-OBzl·HCl (14.9, 47.8 mmoles) by procedures substantially similar to those described above for the preparation of Boc-AlaPro-OBzl, yielding a foam, 22 g. This product crystallized from ethyl acetate to yield Boc-AlaAlaPro-OBzl (7.8 g, mp 120°-121°) in the first crop and 11.1 g (mp 111°-117°) in a second crop. First crop-Anal. Calcd. for C23H33N3O6 (mp 120°-121°): C=61.71%, H=7.45%, N=9.39%. Found: C=61.74%, H=7.56%, and N=9.46%.

Workup

  1. customyielding a foam, 22 g
  2. customThis product crystallized from ethyl acetate

Sources & evidence

ORD record
ord-34d5c8f353b646e4bb11dd28d0c75a11
Source dataset
uspto-grants-1985_02
Patent number
US04499082

Reaction notes

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