Phenylglyoxylic Acid → HCID 58007516, compound

HRID 1094348Notes

Reaction equation

[C:1]1([CH3:20])[CH:6]=[CH:5][C:4]([NH:7][CH2:8][CH2:9][C:10]2[CH:11]=[N:12][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:14][CH:15]=2)=[CH:3][CH:2]=1.[C:21]([C:29](O)=[O:30])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[OH:28][C@H:21]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:29]([N:7]([C:4]1[CH:3]=[CH:2][C:1]([CH3:20])=[CH:6][CH:5]=1)[CH2:8][CH2:9][C:10]1[CH:11]=[N:12][C:13]([C:16]([F:19])([F:17])[F:18])=[CH:14][CH:15]=1)=[O:30]

Participants

Reactant 2

HCID 11915Phenylglyoxylic Acid

HCID 58007505HCID 58007505, compound

Product 1

HCID 58007516HCID 58007516, compoundYield 32.8%

Procedure

In analogy to example 7, steps 1 and 2, p-tolyl-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-amine (200 mg, 0.714 mmol) was coupled to benzoylformic acid (112 mg, 0.746 mmol) and reduced to give the title compound (97 mg, 32.2%) MS m/e: 415.1 [M+H]+ after separation on a chiral column.

Sources & evidence

ORD record: ord-2234395017504ae89c041e396a6cf543
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08133909B2

Reaction notes

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