Sodium cyanoborohydride → HCID 67852557, compound

HRID 2226393Notes

Reaction equation

[NH2:1][C@H:2]([C:4]([N:6]1[CH:14]2[CH:9]([CH2:10][CH2:11][CH2:12][CH2:13]2)[CH2:8][C@H:7]1[C:15]([OH:17])=[O:16])=[O:5])[CH3:3].[O:18]([CH2:25][C:26](=O)[C:27]([OH:29])=[O:28])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([BH3-])#N.[Na+]>>[C:27]([CH:26]([NH:1][C@H:2]([C:4]([N:6]1[CH:14]2[CH:9]([CH2:10][CH2:11][CH2:12][CH2:13]2)[CH2:8][C@H:7]1[C:15]([OH:17])=[O:16])=[O:5])[CH3:3])[CH2:25][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([OH:29])=[O:28]

Participants

Reactant 3

HCID 5003444Sodium cyanoborohydride

HCID 13146116HCID 13146116, compound

HCID 189941262-Oxo-3-phenoxypropanoic acid

Product 1

HCID 67852557HCID 67852557, compound

Procedure

As described in Example 5, condense 1-[(S)-alanyl]octahydroindole-2(S)-carboxylic acid (prepared as described in Example 1) and phenoxypyruvic acid (preparable from ethyl phenoxyacetate and diethyl oxalate, followed by acid catalysed hydrolysis and decarboxylation) with sodium cyanoborohydride to obtain the title compound.

Sources & evidence

ORD record: ord-d60bd014ff4c48759ac1ca6855ad9191
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05348944

Reaction notes

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