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

HRID 420993
ノート
印刷プレビュー

反応式

HRID 420993 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 176Acetic Acid触媒HCID 887Methanol溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-b13ab7cdfa7a40dc82c0afd399429086
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08097623B2

反応ノート

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