Z-Ala-Gly-NH2 → (S)-Benzyl (1-((2-amino-2-oxoethyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate

HRID 1368804Notes

Reaction equation

HRID 1368804 reaction equation
[NH:1]([C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C@@H:2]([C:4]([NH:6][CH2:7][C:8]([NH2:10])=[O:9])=[O:5])[CH3:3].N(C(OC[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=O)[C@H](C(NCC(N)=O)=O)C>CO>[NH:1]([C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12])[C@@H:2]([C:4]([NH:6][CH2:7][C:8]([NH2:10])=[O:9])=[O:5])[CH2:3][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

4

Reactant 2

HCID 7020243Z-Ala-Gly-NH2HCID 11437420Z-D-Ala-Gly-NH2

Product 1

HCID 10937159(S)-Benzyl (1-((2-amino-2-oxoethyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Z-D-Ala-Gly-NH2 (21) (Richman et al., Int. Peptide Protein Res., 25:648-662 (1985), which is hereby incorporated by reference): 1H and 13C NMR data are identical to (8). HRMS (FAB+) MH+ calcd 280.1297 found 280.1298; [α]27D+10.5 (c 0.72, MeOH); lit. [α]D=+10.5.

Sources & evidence

ORD record
ord-fed00d6378ba432e93a2ee09c829c513
Source dataset
uspto-grants-2003_06
Patent number
US06576454B2

Reaction notes

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