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

Participants

Role	Name	HCID	Charge
Reactant	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	HCID 86605289	—
Solvent	Isopropanol heptane	HCID 21225753	—
Product	hydroxy-2-methyl-N-(2,2,3,3,3-pentafluoro-propyl)-malonamide	HCID 87640610	—

Reaction Steps

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).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07211573B2
Source dataset	uspto-grants-2007_05
ORD ID	ord-978331102df643f19a9d8d05231c3110
Source note	uspto-grants-2007_05