2-Oxoglutaric Acid → HCID 13105150, compound

HRID 2418409Notes

Reaction equation

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

Participants

Reactant 3

HCID 512-Oxoglutaric Acid

HCID 83525L-Alanyl-L-proline

HCID 5003444Sodium cyanoborohydride

Product 1

HCID 13105150HCID 13105150, compoundYield 74.8%

Procedure

2-Oxoglutaric acid (1.46 g) and L-alanyl-L-proline (0.37 g) were treated with sodium cyanoborohydride (0.38 g) as described above. Crude N-(1,3-dicarboxypropyl)-L-alanyl-L-proline (0.47 g) was obtained, m.p. 140°-160°. The mass spectrum of silylated material showed an ion at 517 m/e equivalent to the molecular ion for the trisilylated derivative minus methyl (532-15). The nmr spectrum was consistent with structure. Methyl resonances were centered at 1.4 ppm.

Sources & evidence

ORD record: ord-49a42c4f6de0496d8d212ce1d52d00f3
Source dataset: uspto-grants-1984_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04472380

Reaction notes

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