L-Alanyl-L-proline → HCID 53919930, compound

HRID 1758877Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:19])[C:5](=O)[CH2:6][CH2:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=1)[CH3:2].[NH2:20][C@H:21]([C:23]([N:25]1[CH2:32][CH2:31][CH2:30][C@H:26]1[C:27]([OH:29])=[O:28])=[O:24])[CH3:22].C([BH3-])#N.[Na+]>>[CH2:1]([O:3][C:4]([CH:5]([NH:20][C@H:21]([C:23]([N:25]1[CH2:32][CH2:31][CH2:30][C@H:26]1[C:27]([OH:29])=[O:28])=[O:24])[CH3:22])[CH2:6][CH2:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=1)=[O:19])[CH3:2]

Participants

Reactant 3

HCID 83525L-Alanyl-L-proline

HCID 5003444Sodium cyanoborohydride

HCID 18370129HCID 18370129, compound

Product 1

HCID 53919930HCID 53919930, compound

Procedure

In the manner described in Example 26, ethyl-2-oxo-4-(2-naphthyl)-butyrate and L-alanyl-L-proline are condensed in the presence of sodium cyanoborohydride to yield N-[1-ethoxycarbonyl-3-(2-naphthyl)propyl]-L-alanyl-L-proline. The mass spectrum shows a molecular ion at 426 and a peak at 408 (M-18, H2O). The nmr spectrum is consistent with the proposed structure. The elemental analysis indicates a hemihydrate.

Sources & evidence

ORD record: ord-8c70b32e73b84473992dbcb22303b294
Source dataset: uspto-grants-1983_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04374829

Reaction notes

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