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

HRID 1866564노트

반응식

HRID 1866564 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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]+

후처리

  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

출처 및 근거

ORD 기록
ord-06c390cc73a9407485da74ab8b144ecc
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07629358B2

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