3-[3-(1-Ethyl-4,4,6-trimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-7-yl)-4-trifluoromethoxy-phenyl]-acrylic acid tert-butyl ester → 3-[3-(1-Ethyl-4,4,6-trimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-7-yl)-4-trifluoromethoxy-phenyl]-acrylic acid

HRID 2239253Notes

Reaction equation

HRID 2239253 reaction equation
C([O:5][C:6](=[O:36])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[C:11]([C:20]2[C:21]([CH3:35])=[CH:22][C:23]3[C:28]([CH3:30])([CH3:29])[O:27][C:26](=[O:31])[N:25]([CH2:32][CH3:33])[C:24]=3[CH:34]=2)[CH:10]=1)(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[CH2:32]([N:25]1[C:24]2[CH:34]=[C:20]([C:11]3[CH:10]=[C:9]([CH:8]=[CH:7][C:6]([OH:36])=[O:5])[CH:14]=[CH:13][C:12]=3[O:15][C:16]([F:19])([F:17])[F:18])[C:21]([CH3:35])=[CH:22][C:23]=2[C:28]([CH3:30])([CH3:29])[O:27][C:26]1=[O:31])[CH3:33]

Participants

4

Reactant 1

HCID 685832523-[3-(1-Ethyl-4,4,6-trimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-7-yl)-4-trifluoromethoxy-phenyl]-acrylic acid tert-butyl ester

Product 1

HCID 685830023-[3-(1-Ethyl-4,4,6-trimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-7-yl)-4-trifluoromethoxy-phenyl]-acrylic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 0.068 g (0.15 mmol) of Compound 14F in 3 mL of dichloromethane and 2.5 mL of trifluoroacetic acid was stirred at room temperature overnight. The reaction mixture was then concentrated on the rotary evaporator to obtain 3-[3-(1-ethyl-4,4,6-trimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-7-yl)-4-trifluoromethoxy-phenyl]-acrylic acid as a white solid (Compound 14, 0.06 g). MS (electrospray): mass calculated for C257H30F3NO5, 505.13; m/z found 506, [M+H]+.

Workup

  1. concentrationThe reaction mixture was then concentrated on the rotary evaporator

Sources & evidence

ORD record
ord-1782f2c656a74b53b9ac91780270c360
Source dataset
uspto-grants-2010_05
Patent number
US07723326B2

Reaction notes

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