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Potassium Carbonate → Methyl 1-{3-[2-[3-(phenylsulphonylamino)-phenyl]-2-hydroxy-ethylamino]-3-methyl-butyl}-1H-indole-5-carboxylate

HRID 2355247
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HRID 2355247 반응식
C(O[CH:4](O)[C:5]([C:7]1[CH:8]=[C:9]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:10]=[CH:11][CH:12]=1)=[O:6])C.[NH2:24][C:25]([CH3:42])([CH3:41])[CH2:26][CH2:27][N:28]1[C:36]2[C:31](=[CH:32][C:33]([C:37]([O:39][CH3:40])=[O:38])=[CH:34][CH:35]=2)[CH:30]=[CH:29]1.[BH4-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(O)C.C(N(CC)CC)C.C(OCC)(=O)C>[C:17]1([S:14]([NH:13][C:9]2[CH:8]=[C:7]([CH:5]([OH:6])[CH2:4][NH:24][C:25]([CH3:42])([CH3:41])[CH2:26][CH2:27][N:28]3[C:36]4[C:31](=[CH:32][C:33]([C:37]([O:39][CH3:40])=[O:38])=[CH:34][CH:35]=4)[CH:30]=[CH:29]3)[CH:12]=[CH:11][CH:10]=2)(=[O:15])=[O:16])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 4311764Sodium borohydrideHCID 57429080N-[3-(2-ethoxy-2-hydroxyacetyl)-phenyl]-benzenesulphonamideHCID 68453514Methyl 1-(3-amino-3-methyl-butyl)-indole-5-carboxylate

생성물 1

HCID 16659831Methyl 1-{3-[2-[3-(phenylsulphonylamino)-phenyl]-2-hydroxy-ethylamino]-3-methyl-butyl}-1H-indole-5-carboxylate

시약·촉매·용매

3
HCID 8471Triethylamine촉매HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

154 mg (0.46 mmol) N-[3-(2-ethoxy-2-hydroxyacetyl)-phenyl]-benzenesulphonamide (Component I) and 125 mg (0.48 mmol) methyl 1-(3-amino-3-methyl-butyl)-indole-5-carboxylate (Component IV) are dissolved in 10 ml of ethanol and combined with 4 drops of triethylamine. The reaction solution is heated to 80° C. for 17 hours. Then it is cooled to 0° C. and over a period of 2.5 hours 140 mg (3.7 mmol) sodium borohydride are added batchwise. The mixture is stirred for another hour at 0° C. and the reaction solution is then poured into a mixture of 20 ml of saturated aqueous potassium carbonate solution and 50 ml of ethyl acetate. After separation of the organic phase the aqueous phase is extracted with ethyl acetate. The combined organic phases are with washed saturated aqueous saline solution and dried on sodium sulphate. Then the solvent is eliminated in vacuo and the residue is chromatographed on silica gel (DCM/methanol=100:0:0→9:1).

후처리

  1. additionare added batchwise
  2. customAfter separation of the organic phase the aqueous phase
  3. extractionis extracted with ethyl acetate
  4. customdried on sodium sulphate
  5. customthe residue is chromatographed on silica gel (DCM/methanol=100:0:0→9:1)

출처 및 근거

ORD 기록
ord-939f452e2a78453f9dbf29b55708be13
출처 데이터셋
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07754756B2

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