Hexane → HCID 178464143, compound

HRID 1170450Notes

Reaction equation

HRID 1170450 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1([OH:34])[C:17]2[C:12](=[CH:13][C:14]([I:22])=[CH:15][C:16]=2[C:18]([F:21])([F:20])[F:19])[N:11]([CH2:23][C@H:24]2[CH2:27][C@H:26]([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[CH2:25]2)[C:10]1=[O:33].[CH3:35][O:36][C@@H:37]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:38]([OH:40])=[O:39].CCCCCC>C(OCC)(=O)C>[CH3:35][O:36][C@@H:37]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:38]([O-:40])=[O:39].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1([OH:34])[C:17]2[C:12](=[CH:13][C:14]([I:22])=[CH:15][C:16]=2[C:18]([F:20])([F:21])[F:19])[N:11]([CH2:23][C@H:24]2[CH2:25][C@H:26]([N:28]([CH2:29][CH3:30])[CH2:31][CH3:32])[CH2:27]2)[C:10]1=[O:33]

Participants

6

Reactant 3

HCID 8058HexaneHCID 643325(+)-Methoxyphenylacetic acidHCID 178464143HCID 178464143, compound

Product 2

HCID 6931594(S)-methoxyphenylacetateHCID 178464143HCID 178464143, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
6 °C

Procedure

To a solution of 3-(2-chloro-6-fluorophenyl)-1-[trans-3-(diethylamino)-cyclobutylmethyl]-4-trifluoromethyl-3-hydroxy-6-iodo-1,3-dihydro-2H-indol-2-one (3.60 g, 5.89 mmol) in ethyl acetate (50 mL) was added (S)-α-methoxyphenylacetic acid (550 mg), and the mixture was heated to 6° C. and stirred for 1 hour. Then, the mixture was stirred at room temperature for 1 hour, and thereto was added hexane (10 mL), and the mixture was stirred for additional 30 minutes at room temperature. The precipitated solid was filtered (1.41 g). The solid was recrystallized from ethyl acetate (20 mL)/hexane (3.0 ml) to give (S)-methoxyphenylacetate of 3-(2-chloro-6-fluorophenyl)-1-[trans-3-(diethylamino)-cyclobutylmethyl]-4-trifluoromethyl-3-hydroxy-6-iodo-1,3-dihydro-2H-indol-2-one (970 mg). The resulting compound was converted to its nonsalt form. Thus, the titled compound (650 mg, 98% ee, 18% y.) was obtained.

Workup

  1. stirringThen, the mixture was stirred at room temperature for 1 hour
  2. stirringthe mixture was stirred for additional 30 minutes at room temperature
  3. filtrationThe precipitated solid was filtered (1.41 g)
  4. customThe solid was recrystallized from ethyl acetate (20 mL)/hexane (3.0 ml)

Sources & evidence

ORD record
ord-ab51b5532473424b8defa37bdae50992
Source dataset
uspto-grants-2010_11
Patent number
US07825155B2

Reaction notes

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