4,3'-Dichloro-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]-biphenyl-3-carboxylic acid methyl ester → 4,3'-Dichloro-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]-biphenyl-3-carboxylic acid

HRID 2386771Notes

Reaction equation

HRID 2386771 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH3:38])[C:19]([C:25]3[CH:26]=[CH:27][C:28]4[O:33][CH2:32][C:31](=[O:34])[N:30]([CH2:35][CH3:36])[C:29]=4[CH:37]=3)([OH:24])[C:20]([F:23])([F:22])[F:21])=[C:14]([Cl:39])[CH:13]=2)[CH:8]=[CH:9][C:10]=1[Cl:11])=[O:4]>CCCCCCC>[Cl:11][C:10]1[CH:9]=[CH:8][C:7]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH3:38])[C:19]([C:25]3[CH:26]=[CH:27][C:28]4[O:33][CH2:32][C:31](=[O:34])[N:30]([CH2:35][CH3:36])[C:29]=4[CH:37]=3)([OH:24])[C:20]([F:22])([F:21])[F:23])=[C:14]([Cl:39])[CH:13]=2)=[CH:6][C:5]=1[C:3]([OH:4])=[O:2]

Participants

3

Reactant 1

HCID 675465414,3'-Dichloro-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]-biphenyl-3-carboxylic acid methyl ester

Product 1

HCID 666972104,3'-Dichloro-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]-biphenyl-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

In analogy to Example 56, step 6, 4,3′-Dichloro-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]-biphenyl-3-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)=566.2 [M−H+].

Workup

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

Sources & evidence

ORD record
ord-603eb2cb68eb4c9dba9ab4eafc53e128
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

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