Trifluoroacetic acid → t-Butyl [(RS)-2-[[(S)-2-[(benzyloxy)carbonyl]-1-carbamoylethyl]-carbamoyl]propyl]carbamate

HRID 327518Notes

Reaction equation

HRID 327518 reaction equation
C(O[C:6]([NH:8][C@H:9]([C:21]([NH2:23])=[O:22])[CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[O:7])(C)(C)C.FC(F)(F)C(O)=O.[C:31]([O:35][C:36]([NH:38][CH2:39][CH:40](C)[C:41](O)=O)=[O:37])([CH3:34])([CH3:33])[CH3:32]>>[CH2:14]([O:13][C:11]([CH2:10][C@H:9]([NH:8][C:6]([CH:40]([CH3:41])[CH2:39][NH:38][C:36](=[O:37])[O:35][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:7])[C:21](=[O:22])[NH2:23])=[O:12])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 41926403-((tert-Butoxycarbonyl)amino)-2-methylpropanoic acidHCID 10615806Benzyl (S)-3-(1-t-butoxyformamido)succinamate

Product 1

HCID 86747430t-Butyl [(RS)-2-[[(S)-2-[(benzyloxy)carbonyl]-1-carbamoylethyl]-carbamoyl]propyl]carbamate

Procedure

Benzyl (S)-3-(1-t-butoxyformamido)succinamate was deprotected using trifluoroacetic acid and then coupled with DL-N-(t-butoxycarbonyl)-2-methyl-β-alanine to yield t-Butyl [(RS)-2-[[(S)-2-[(benzyloxy)carbonyl]-1-carbamoylethyl]-carbamoyl]propyl]carbamate, m.p. 135°-136° C.

Sources & evidence

ORD record
ord-e776114efa2e4d789633aa3d83df596d
Source dataset
uspto-grants-1993_12
Patent number
US05273982

Reaction notes

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