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Methanol → 4-(5-Cyclopentyloxycarbonylamino-1H-indol-3-ylmethyl)-3-methoxy-benzoic acid

HRID 1739583
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HRID 1739583 반응식
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([NH:20][C:21]([O:23][CH:24]4[CH2:28][CH2:27][CH2:26][CH2:25]4)=[O:22])[CH:18]=3)[NH:13][CH:12]=2)=[C:6]([O:29][CH3:30])[CH:5]=1.CO.O1CCCC1.O.[OH-].[Li+]>O>[CH:24]1([O:23][C:21]([NH:20][C:17]2[CH:18]=[C:19]3[C:14](=[CH:15][CH:16]=2)[NH:13][CH:12]=[C:11]3[CH2:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:31])=[O:2])=[CH:5][C:6]=2[O:29][CH3:30])=[O:22])[CH2:25][CH2:26][CH2:27][CH2:28]1
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참가 물질

6

반응물 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 23365866HCID 23365866, 화합물

생성물 1

HCID 146268444-(5-Cyclopentyloxycarbonylamino-1H-indol-3-ylmethyl)-3-methoxy-benzoic acid수율 92.3%

시약·촉매·용매 1

HCID 962
Water
용매

실험 절차

To a solution of 4-[5-(cyclopentyloxycarbonyl)amino-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid methylester (0.82 grams, 1.95 mmol) in a 2:2:1 ratio of methanol:tetrahydrofuran:water (30 mL) was added lithium hydroxide monohydrate (0.41 grams, 0.73 mmol). The resulting solution was stirred for 12 hours at room temperature. The solution was concentrated, and the crude product treated with 1 hydrochloric acid (aq). The product was collected via filtration. Chromatography on silica gel (1:1 hexanes:ethyl acetate→5% methanol:methylene chloride) gave 4-[5-(cyclopentyloxycarbonyl)amino-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid (0.735 grams, 92 yield).

후처리

  1. concentrationThe solution was concentrated
  2. additionthe crude product treated with 1 hydrochloric acid (aq)
  3. filtrationThe product was collected via filtration

출처 및 근거

ORD 기록
ord-d59adf0f02724cc588e8438d1a33877b
출처 데이터셋
uspto-grants-1999_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05965745

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