Sodium hydride → HCID 68592504, compound

HRID 736921Notes

Reaction equation

[H-].[Na+].C(OP([CH2:11][C:12]([N:14]1[C@H:18]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:17][O:16][C:15]1=[O:26])=[O:13])(=O)OCC)C.[NH2:27][C:28]1[C:35]([C:36]([F:39])([F:38])[F:37])=[CH:34][C:31]([CH:32]=O)=[CH:30][C:29]=1[Cl:40].[NH4+].[Cl-]>C1COCC1>[NH2:27][C:28]1[C:35]([C:36]([F:37])([F:38])[F:39])=[CH:34][C:31](/[CH:32]=[CH:11]/[C:12]([N:14]2[C@H:18]([CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:17][O:16][C:15]2=[O:26])=[O:13])=[CH:30][C:29]=1[Cl:40]

Participants

Conditions

Temperature: 35 °C

Procedure

Under a nitrogen atmosphere 3.93 g (90.0 mmol) of NaH (55% in mineral oil) were added batchwise to a solution of 31.98 g (90.0 mmol) of diethyl[2-((R)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-oxo-ethyl]-phosphonate in 400 mL of THF. The reaction mixture was stirred for 30 min at RT and for a further 35 min at 35° C. After the development of gas had ended, 16.0 g (71.5 mmol) of 4-amino-3-chloro-5-trifluoromethyl-benzaldehyde, dissolved in 50 mL THF, were added dropwise and stirred for a further 12 h at RT. The reaction solution was combined with saturated NH4Cl solution, the mixture was extracted exhaustively with EtOAc and the combined extracts were dried and evaporated down i. vac. The residue remaining was purified by chromatography on silica gel. The desired product was obtained in the form of a yellow oil.

Workup

additionwere added dropwise
stirringstirred for a further 12 h at RT
extractionthe mixture was extracted exhaustively with EtOAc
customthe combined extracts were dried
customevaporated down i
customThe residue remaining was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-2cffe4f1f2494c369df60be428276b61
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595312B2

Reaction notes

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