3'-Chloro-4'-[2-(4-ethyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-3-fluoro-biphenyl-4-carboxylic acid methyl ester → 3'-Chloro-4'-[2-(4-ethyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-3-fluoro-biphenyl-4-carboxylic acid

HRID 2386769Notes

Reaction equation

HRID 2386769 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]([CH3:37])[C:18]([C:24]3[CH:25]=[CH:26][C:27]4[O:32][CH2:31][C:30](=[O:33])[N:29]([CH2:34][CH3:35])[C:28]=4[CH:36]=3)([OH:23])[C:19]([F:22])([F:21])[F:20])=[C:13]([Cl:38])[CH:12]=2)=[CH:7][C:6]=1[F:39])=[O:4]>CCCCCCC>[Cl:38][C:13]1[CH:12]=[C:11]([C:8]2[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[C:6]([F:39])[CH:7]=2)[CH:16]=[CH:15][C:14]=1[CH:17]([CH3:37])[C:18]([C:24]1[CH:25]=[CH:26][C:27]2[O:32][CH2:31][C:30](=[O:33])[N:29]([CH2:34][CH3:35])[C:28]=2[CH:36]=1)([OH:23])[C:19]([F:22])([F:21])[F:20]

Participants

3

Reactant 1

HCID 675465023'-Chloro-4'-[2-(4-ethyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-3-fluoro-biphenyl-4-carboxylic acid methyl ester

Product 1

HCID 666972013'-Chloro-4'-[2-(4-ethyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-3-fluoro-biphenyl-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

In analogy to Example 56, step 6, 3′-chloro-4′-[2-(4-ethyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-3-fluoro-biphenyl-4-carboxylic acid methyl ester was hydrolyzed (3 h, 65° C.). The product was treated with heptane for 17 h, filtered and dried to give the title compound as a white solid. MS (m/e, ISP neg. ion)=550.2 [M−H+].

Workup

  1. custom(3 h, 65° C.)
  2. filtrationfiltered
  3. customdried

Sources & evidence

ORD record
ord-032ad878f1f54e57baeb92adeca5fa17
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

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