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Hexane → HCID 178464143, 화합물

HRID 1170450
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HRID 1170450 반응식
[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]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

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

생성물 2

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate
용매

반응 조건

온도
6 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ab51b5532473424b8defa37bdae50992
출처 데이터셋
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07825155B2

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