Triethylamine → (S)-3-(isopropoxycarbonyl-aminomethyl)-5-methyl-hexanoic acid

HRID 561348노트

반응식

HRID 561348 반응식
[CH:1]([O:4][C:5]([CH:7]([NH2:17])[CH:8]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:9][C:10]([OH:12])=[O:11])=[O:6])([CH3:3])[CH3:2].C(N(CC)CC)C>O.C(O)(C)C>[CH:1]([O:4][C:5]([CH:7]([NH2:17])[C@@H:8]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:9][C:10]([OH:12])=[O:11])=[O:6])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 8471TriethylamineHCID 866477143-(Isopropoxycarbonyl-amino-methyl)-5-methyl-hexanoic acid

생성물 1

HCID 86647713(S)-3-(isopropoxycarbonyl-aminomethyl)-5-methyl-hexanoic acid수율 61.1%

시약·촉매·용매 1

HCID 21889133Propan-2-ol--water (1/1)용매

반응 조건

온도
57.5 °C

실험 절차

A 500 ml three-necked round-bottom flask, under nitrogen atmosphere, is added with raceme 3-(isopropoxycarbonyl-amino-methyl)-5-methyl-hexanoic acid (44.2 g, 0.180 moles), triethylamine (8.20 g, 0.081 moles) and (S)-(−)-phenyl-ethylamine (12.00 g; 0.099 moles) in a 95:5 water/isopropanol mixture (200 ml) heated at 55-60° C. The mixture is spontaneously left to cool to room temperature, then it is cooled to 0-5° C. for at least 1 h. The solid is filtered off and washed with cool water (2×20 ml) and then with cool toluene (4×20 ml), it is dried in oven at 55-60° C. for 16-18 h. 27.0 g of white solid are obtained with an enantiomer ratio of 99:1.

후처리

  1. waitThe mixture is spontaneously left
  2. temperatureto cool to room temperature
  3. temperatureit is cooled to 0-5° C. for at least 1 h
  4. filtrationThe solid is filtered off
  5. washwashed with cool water (2×20 ml)
  6. dry with materialwith cool toluene (4×20 ml), it is dried in oven at 55-60° C. for 16-18 h

출처 및 근거

ORD 기록
ord-045b0b793f3a4b92b51534b38c469830
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063244B2

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