Hydrochloric Acid → [3-((2R)-2-{[(1R)-1-Phenylethyl]amino}propyl)phenyl]acetic acid

HRID 1866564ノート

反応式

HRID 1866564 の反応式
[OH-].[Li+].Cl.C[O:5][C:6](=[O:26])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][C@H:15]([NH:17][C@@H:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH3:19])[CH3:16])[CH:9]=1.Cl>CO>[C:20]1([C@H:18]([NH:17][C@H:15]([CH3:16])[CH2:14][C:10]2[CH:9]=[C:8]([CH2:7][C:6]([OH:26])=[O:5])[CH:13]=[CH:12][CH:11]=2)[CH3:19])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 46938908methyl[3-((2R)-2-{[(1R)-1-phenyl-ethyl]-amino}-propyl)-phenyl]-acetate hydrochloride

生成物 1

HCID 58907418[3-((2R)-2-{[(1R)-1-Phenylethyl]amino}propyl)phenyl]acetic acid収率 91%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Lithium hydroxide solution (1M in water, 90 mL, 90 mmol) was added to a solution of methyl[3-((2R)-2-{[(1R)-1-phenyl-ethyl]-amino}-propyl)-phenyl]-acetate hydrochloride (preparation 26), (13.5 g, 43.5 mmol) in methanol (200 mL) and the mixture was stirred at room temperature for 18 hours. 1M Hydrochloric acid (90 mL) was then added to the reaction mixture and the methanol removed in vacuo. The resulting precipitate was filtered off and washed with water (20 mL) and a mixture of ethanol/diethyl ether, 20:80, to afford the title compound as a solid in 91% yield, 11.8 g 1H NMR (400 MHz, CD3OD) δ: 7.52-7.45 (5H, m), 7.22-7.18 (2H, m), 7.19 (1H, s), 6.92 (1H, d), 4.56-4.48 (1H, q), 3.46 (2H, s), 3.26-3.13 (2H, m), 2.66-2.62 (1H, m), 1.62 (3H, d), 1.16 (3H, d) ppm; LRMS ESI m/z 298 [M+H]+

後処理

  1. customthe methanol removed in vacuo
  2. filtrationThe resulting precipitate was filtered off
  3. washwashed with water (20 mL)
  4. additiona mixture of ethanol/diethyl ether, 20:80

出典と根拠

ORDレコード
ord-06c390cc73a9407485da74ab8b144ecc
出典データセット
uspto-grants-2009_12
特許番号
US07629358B2

反応ノート

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