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

HRID 252185ノート

反応式

HRID 252185 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-5304b3e7cee440f48200f15ab793e29e
出典データセット
uspto-grants-2011_01
特許番号
US07868010B2

反応ノート

読み込み中…