L-Alanyl-L-proline → HCID 12718473, compound

HRID 1758851Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][C:12](=O)[C:13]([OH:15])=[O:14])=[CH:2]1.[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+]>>[C:13]([CH:12]([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])[CH2:11][CH2:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)([OH:15])=[O:14]

Participants

Reactant 3

HCID 83525L-Alanyl-L-proline

HCID 5003444Sodium cyanoborohydride

HCID 18964897HCID 18964897, compound

Product 1

HCID 12718473HCID 12718473, compound

Procedure

In the manner described in example 24, 4-(3-indolyl)-2-oxobutyric acid and L-alanyl-L-proline are condensed in the presence of sodium cyanoborohydride to yield N-[1-carboxy-3-(3-indolyl)propyl]L-alanyl-L-proline. The mass spectrum of the trisilyated material shows a molecular ion at 603 m/e and a M+ -15 peak at 588 m/e.

Sources & evidence

ORD record: ord-7c307ec9bfc946be8231119522c8b899
Source dataset: uspto-grants-1983_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04374829

Reaction notes

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