Methanol → [[3-(2-amino-1,2-dioxoethyl)-1-[(4-fluorophenyl)methyl]-2-methyl-1H-indol-4-yl]oxy]acetic acid

HRID 581134ノート

反応式

HRID 581134 の反応式
C[O:2][C:3](=[O:29])[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8]([C:24](=[O:28])[C:25]([NH2:27])=[O:26])=[C:9]([CH3:23])[N:10]2[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1.[OH-].[Na+].CO.C(OCC)(=O)C>O>[NH2:27][C:25](=[O:26])[C:24]([C:8]1[C:7]2[C:11](=[CH:12][CH:13]=[CH:14][C:6]=2[O:5][CH2:4][C:3]([OH:29])=[O:2])[N:10]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)[C:9]=1[CH3:23])=[O:28]

参加物

6

反応物 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 10524900HCID 10524900、化合物

生成物 1

HCID 9821429[[3-(2-amino-1,2-dioxoethyl)-1-[(4-fluorophenyl)methyl]-2-methyl-1H-indol-4-yl]oxy]acetic acid収率 81.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 767 mg (1.9 mmol) of [[3-(2-amino-1,2-dioxoethyl)-1-[(4-fluorophenyl)methyl]-2-methyl-1H-indol-4-yl]oxy]acetic acid methyl ester, 10 mL of 1N NaOH and 30 mL of MeOH was heated to maintain reflux for 0.67 hours, cooled to room temperature and stirred 1 hour. Ethyl acetate and water were added and the aqueous layer separated, made acidic to pH 2-3 with 1N HCl and the mixture extracted with ethyl acetate two times. The combined ethyl acetate extracts were dried (MgSO4) and concentrated. The remaining solid was washed with a small volume of ethyl acetate to give 593 mg (81% yield) of [[3-(2-amino-1,2-dioxoethyl)-1-[(4-fluorophenyl)methyl]-2-methyl-1H-indol-4-yl]oxy]acetic acid, mp, 244-247° C.

後処理

  1. temperaturewas heated
  2. temperatureto maintain
  3. temperaturereflux for 0.67 hours
  4. customthe aqueous layer separated
  5. extractionthe mixture extracted with ethyl acetate two times
  6. dry with materialThe combined ethyl acetate extracts were dried (MgSO4)
  7. concentrationconcentrated
  8. washThe remaining solid was washed with a small volume of ethyl acetate

出典と根拠

ORDレコード
ord-3ce229f7c4aa4d5bbe8739d3c177f4e9
出典データセット
uspto-grants-1999_07
特許番号
US05919810

反応ノート

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