N-[(6R,7S)-2-fluoro-9-(2-hydroxy-ethyl)-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl]-2-hydroxy-2-methyl-N-(2,2,3,3,3-pentafluoro-propyl)-malonamide → hydroxy-2-methyl-N-(2,2,3,3,3-pentafluoro-propyl)-malonamide

HRID 1348650Notes

Reaction equation

HRID 1348650 reaction equation
FC1C=CC2O[C@H](C)[C@H]([N:13]([CH2:22][C:23]([F:29])([F:28])[C:24]([F:27])([F:26])[F:25])[C:14](=[O:21])[C:15]([OH:20])([CH3:19])[C:16]([NH2:18])=[O:17])C(=O)N(CCO)C=2C=1>C(O)(C)C.CCCCCCC>[OH:20][C:15]([CH3:19])([C:16]([NH2:18])=[O:17])[C:14]([NH:13][CH2:22][C:23]([F:28])([F:29])[C:24]([F:27])([F:26])[F:25])=[O:21]

Participants

3

Reactant 1

HCID 86605289N-[(6R,7S)-2-fluoro-9-(2-hydroxy-ethyl)-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl]-2-hydroxy-2-methyl-N-(2,2,3,3,3-pentafluoro-propyl)-malonamide

Product 1

HCID 87640610hydroxy-2-methyl-N-(2,2,3,3,3-pentafluoro-propyl)-malonamide

Reagents, catalysts & solvents 1

HCID 21225753Isopropanol heptaneSolvent

Procedure

0.31 g (1.0 mmol) N-[(6R,7S)-2-Fluoro-9-(2-hydroxy-ethyl)-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl]-2-hydroxy-2-methyl-N-(2,2,3,3,3-pentafluoro-propyl)-malonamide epimers were separated by chromatography on Chiralpak AD with isopropanol/heptane 15:85 to yield 0.11 g N-[(6R,7S)-2-fluoro-9-(2-hydroxy-ethyl)-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl]-2-(R or S)-hydroxy-2-methyl-N-(2,2,3,3,3-pentafluoro-propyl)-malonamide, entity A, MS m/e (%): 502.3 (M+H+, 100) and 0.08 g N-[(6R,7S)-2-fluoro-9-(2-hydroxy-ethyl)-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl]-2-(R or S)-hydroxy-2-methyl-N-(2,2,3,3,3-pentafluoro-propyl)-malonamide, entity B, MS m/e (%): 502.1 (M+H+, 100).

Sources & evidence

ORD record
ord-978331102df643f19a9d8d05231c3110
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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