L-Alanyl-L-proline → HCID 54172182, compound

HRID 1758875Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:16])[C:5](=O)[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:14])[CH3:2].[NH2:17][C@H:18]([C:20]([N:22]1[CH2:29][CH2:28][CH2:27][C@H:23]1[C:24]([OH:26])=[O:25])=[O:21])[CH3:19].C([BH3-])#N.[Na+]>>[CH2:1]([O:3][C:4]([CH:5]([NH:17][C@H:18]([C:20]([N:22]1[CH2:29][CH2:28][CH2:27][C@H:23]1[C:24]([OH:26])=[O:25])=[O:21])[CH3:19])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:14])=[O:16])[CH3:2]

Participants

Reactant 3

HCID 83525L-Alanyl-L-proline

HCID 5003444Sodium cyanoborohydride

HCID 20445815HCID 20445815, compound

Product 1

HCID 54172182HCID 54172182, compound

Procedure

In the manner described in Example 26, ethyl-2-oxo-4-(2-chlorophenyl)butyrate and L-alanyl-L-proline are condensed in the presence of sodium cyanoborohydride to yield N-[1-ethoxycarbonyl-3-(2-chlorophenyl)-propyl]-L-alanyl-L-proline. The mass spectrum shows a peak at 411, (M+1), and a strong peak at 392, (M-18).

Sources & evidence

ORD record: ord-95f05e6df9f146c2ab2bfb936a080a0a
Source dataset: uspto-grants-1983_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04374829

Reaction notes

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