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Water → 5-(4-tert-Butylphenyl)-3-[(ethoxycarbonylmethylmethylamino)methyl]-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester

HRID 420993
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HRID 420993 반응식
Cl.[CH2:2]([O:4][C:5](=[O:9])[CH2:6][NH:7][CH3:8])[CH3:3].[CH2:10]([O:12][C:13]([C:15]1[N:16]([C:36]2[CH:41]=[CH:40][C:39]([O:42][CH:43]([CH3:45])[CH3:44])=[CH:38][CH:37]=2)[C:17]2[C:22]([C:23]=1C=O)=[CH:21][C:20]([C:26]1[CH:31]=[CH:30][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:28][CH:27]=1)=[CH:19][CH:18]=2)=[O:14])[CH3:11].[BH3-][C:47]#N.[Na+].O>CO.C(O)(=O)C>[CH2:10]([O:12][C:13]([C:15]1[N:16]([C:36]2[CH:41]=[CH:40][C:39]([O:42][CH:43]([CH3:45])[CH3:44])=[CH:38][CH:37]=2)[C:17]2[C:22]([C:23]=1[CH2:8][N:7]([CH2:6][C:5]([O:4][CH2:2][CH3:3])=[O:9])[CH3:47])=[CH:21][C:20]([C:26]1[CH:31]=[CH:30][C:29]([C:32]([CH3:35])([CH3:33])[CH3:34])=[CH:28][CH:27]=1)=[CH:19][CH:18]=2)=[O:14])[CH3:11]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 962WaterHCID 171173Ethyl N-methylaminoacetate hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 866288225-(4-tert-Butylphenyl)-3-formyl-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester

생성물 1

HCID 666577165-(4-tert-Butylphenyl)-3-[(ethoxycarbonylmethylmethylamino)methyl]-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester

시약·촉매·용매 2

HCID 176Acetic Acid촉매HCID 887Methanol용매

실험 절차

N-Methyl glycine ethyl ester hydrochloride (255 mg, 1.66 mmol) was added to a suspension of 5-(4-tert-butylphenyl)-3-formyl-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester (400 mg, 0.83 mmol; see step (c) above) in MeOH (20 mL) and the pH was adjusted to 6 by the addition of a few drops of glacial acetic acid. After 1 h at rt, NaCNBH3 (75 mg, 1.18 mmol) was added and the mixture was stirred at rt for 24 h, poured into H2O and extracted with EtOAc. The combined extracts were washed with H2O and brine, dried (Na2SO4), concentrated and purified by chromatography to give the sub-title compound. Yield 400 mg (87%).

후처리

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed with H2O and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified by chromatography

출처 및 근거

ORD 기록
ord-b13ab7cdfa7a40dc82c0afd399429086
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08097623B2

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