2-Hydroxy-2-methyl-N-(3,3,3-trifluoro-propyl)-malonamic acid → HCID 131726361, compound

HRID 1348658Notes

Reaction equation

HRID 1348658 reaction equation
[OH:1][C:2]([CH3:15])([C:6]([NH:8][CH2:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[O:7])[C:3](O)=[O:4].[NH2:16][C@@H]1C(=O)N(CC(F)(F)F)C2C=C(F)C=CC=2O[C@@H]1C>>[OH:1][C:2]([CH3:15])([C:6]([NH:8][CH2:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[O:7])[C:3]([NH2:16])=[O:4]

Participants

3

Reactant 2

HCID 210914092-Hydroxy-2-methyl-N-(3,3,3-trifluoro-propyl)-malonamic acidHCID 21091439HCID 21091439, compound

Product 1

HCID 131726361HCID 131726361, compound

Procedure

N-[(6R,7S)-2-Fluoro-6-methyl-8-oxo-9-(2,2,2-trifluoro-ethyl)-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl]-2-(R or S)-hydroxy-2-methyl-N′-(3,3,3-trifluoro-propyl)-malonamide was obtained as mixture of epimers according to the procedures described for example 2b using racemic 2-hydroxy-2-methyl-N-(3,3,3-trifluoro-propyl)-malonamic acid and (6R,7S)-7-amino-2-fluoro-6-methyl-9-(2,2,2-trifluoro-ethyl)-6,7-dihydro-9H-5-oxa-9-aza-benzocyclohepten-8-one. The epimers were separated by chromatography on Chiralpak AD using ethanol/heptane 15:85 to yield (−)-N-[(6R,7S)-2-fluoro-6-methyl-8-oxo-9-(2,2,2-trifluoro-ethyl)-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl]-2-(R or S)-hydroxy-2-methyl-N′-(3,3,3-trifluoro-propyl)-malonamide, entity A, MS m/e (%): 504.0 (M+H+, 100), as first eluting fraction, and (−)-N-[(6R,7S)-2-fluoro-6-methyl-8-oxo-9-(2,2,2-trifluoro-ethyl)-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl]-2-(R or S)-hydroxy-2-methyl-N′-(3,3,3-trifluoro-propyl)-malonamide, entity B, as second eluting fraction, MS m/e (%): 504.0 (M+H+, 100).

Workup

  1. customThe epimers were separated by chromatography on Chiralpak AD

Sources & evidence

ORD record
ord-57b8c6b2f32c403fb939358780bf9220
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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