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Methyl chloroformate → 1-(3,5-difluorophenyl)-2-(2,3-dihydro-6-methoxycarbonylmethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropan-1-one

HRID 1274864
Notes
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Reaction equation

HRID 1274864 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[F:11][C:12]1[CH:13]=[C:14]([C:19](=[O:37])[C:20]([N:23]2[C:28](=[O:29])[C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[C:26]([CH3:36])[O:25][CH2:24]2)([CH3:22])[CH3:21])[CH:15]=[C:16]([F:18])[CH:17]=1.Cl[C:39]([O:41][CH3:42])=[O:40]>O1CCCC1>[F:11][C:12]1[CH:13]=[C:14]([C:19](=[O:37])[C:20]([N:23]2[C:28](=[O:29])[C:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[C:26]([CH2:36][C:39]([O:41][CH3:42])=[O:40])[O:25][CH2:24]2)([CH3:22])[CH3:21])[CH:15]=[C:16]([F:18])[CH:17]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 2733832Lithium HexamethyldisilazideHCID 221182601-(3,5-difluorophenyl)-2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methyl-propan-1-one

Product 1

HCID 221182741-(3,5-difluorophenyl)-2-(2,3-dihydro-6-methoxycarbonylmethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropan-1-oneYield 11.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

Lithium bis(trimethylsilyl)amide (1.5 ml of 1.0M solution) was added to a solution of 1-(3,5-difluorophenyl)-2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methyl-propan-1-one (0.5 g) in tetrahydrofuran, under an inert atmosphere at -5° C. After stirring for 0.5 hours, methyl chloroformate (1.22 g) was added and the solution allowed to warm to 20° C. After 18 hours, the solution was poured onto water, extracted (ether) and evaporated. Purification by dry column chromatography on silica gel, eluting with hexane/ethyl acetate (4:1), gave 1-(3,5-difluorophenyl)-2-(2,3-dihydro-6-methoxycarbonylmethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropan-1-one (Compound 700, 0.065 g), NMR 1.5 (s,6H), 3.1 (s,2H), 3.6 (s,3H), 5.4 (s,2H), 6.8 (m,1H), 7.0 (m,2H), 7.2 (m,3H), 7.5 (d,2H).

Workup

  1. waitAfter 18 hours
  2. additionthe solution was poured onto water
  3. extractionextracted (ether)
  4. customevaporated
  5. customPurification
  6. customby dry column chromatography on silica gel
  7. washeluting with hexane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-750a4d3e084b47a492ee5e71e12e0be9
Source dataset
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06159902

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes