Potassium Hydroxide → [4-(4-tert-Butoxycarbonylaminobutyl)phenoxy]acetic acid

HRID 1296573ノート

反応式

HRID 1296573 の反応式
C[O:2][C:3](=[O:24])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:8][CH:7]=1.[OH-].[K+]>CO>[C:20]([O:19][C:17]([NH:16][CH2:15][CH2:14][CH2:13][CH2:12][C:9]1[CH:8]=[CH:7][C:6]([O:5][CH2:4][C:3]([OH:24])=[O:2])=[CH:11][CH:10]=1)=[O:18])([CH3:23])([CH3:21])[CH3:22]

参加物

4

反応物 2

HCID 14797Potassium HydroxideHCID 21031129[4-(4-tert-Butoxycarbonylaminobutyl)phenoxy]acetic acid methyl ester

生成物 1

HCID 22054428[4-(4-tert-Butoxycarbonylaminobutyl)phenoxy]acetic acid収率 97.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of [4-(4-tert-butoxycarbonylaminobutyl)phenoxy]acetic acid methyl ester 32 (1.28 g, 3.78 mmol) in methanol (80 mL) was added with crushed potassium hydroxide (2.50 g, 85%, 37.8 mmol) and the mixture was stirred at room temperature for 5 h. Solvent was removed by rotary evaporation. The residue was taken up in water and acidified to pH ˜1 with 6N aqueous HCl, and extracted with dichloromethane. The combined organics were washed with brine, dried over Na2SO4, and concentrated to complete dryness to afford the desired product 33 as a white solid (1.19 g, 97% yield). 1H NMR (300 MHz, CD3OD) δ 1.41 (s, 9H), 1.42–1.70 (m, 4H), 2.45–2.60 (m, 2H), 3.00–3.20 (m, 2H), 4.60 (s, 2H), 6.80 (d, 2H), 7.08 (d, 2H). m/z (ESI): 322 [C17H25NO5—H]−.

後処理

  1. customSolvent was removed by rotary evaporation
  2. extractionextracted with dichloromethane
  3. washThe combined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-47cd4aee99a9443cb0012b0972d624de
出典データセット
uspto-grants-2007_07
特許番号
US07247637B2

反応ノート

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