L-Alanyl-L-proline → HCID 54060932, compound

HRID 1758876Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:16])[C:5](=O)[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)[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][C:11]([F:14])=[CH:10][CH:9]=1)=[O:16])[CH3:2]

Participants

Reactant 3

HCID 83525L-Alanyl-L-proline

HCID 5003444Sodium cyanoborohydride

HCID 18370942HCID 18370942, compound

Product 1

HCID 54060932HCID 54060932, compound

Procedure

In the manner described in Example 26, ethyl-2-oxo-4-(4-fluoro-phenyl)butyrate and L-alanyl-L-proline are condensed in the presence of sodium cyanoborohydride to yield N-[1-ethoxycarbonyl-3-(4-fluorophenyl)-propyl]-L-alanyl-L-proline. The mass spectrum shows a molecular ion at 394, and strong peaks at 376 (M-18, H2O) and 375 (M-19, F). The nmr spectrum is consistent with the proposed structure. Elemental analysis indicates a sesquihydrate.

Sources & evidence

ORD record: ord-374ecc5c6d244b0ea8260efb19300268
Source dataset: uspto-grants-1983_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04374829

Reaction notes

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