Triphenylphosphine → (S)-2-ethoxy-3-(4-{2-[4-(phenylsulfanyl)phenyl]ethoxy}phenyl)propanoic acid ethyl ester

HRID 987325노트

반응식

HRID 987325 반응식
[C:1]1([S:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:18]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.[CH2:54]([O:56][C@@H:57]([CH2:61][C:62]1[CH:67]=[CH:66][C:65](O)=[CH:64][CH:63]=1)[C:58]([OH:60])=[O:59])[CH3:55]>ClCCl>[CH2:17]([O:60][C:58](=[O:59])[C@@H:57]([O:56][CH2:54][CH3:55])[CH2:61][C:62]1[CH:67]=[CH:66][C:65]([O:16][CH2:15][CH2:14][C:11]2[CH:12]=[CH:13][C:8]([S:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:9][CH:10]=2)=[CH:64][CH:63]=1)[CH3:18]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 9837207(2S)-2-Ethoxy-3-(4-hydroxyphenyl)propanoic acidHCID 135676692-(4-Phenylsulfanylphenyl)ethanol

생성물 1

HCID 54503267(S)-2-ethoxy-3-(4-{2-[4-(phenylsulfanyl)phenyl]ethoxy}phenyl)propanoic acid ethyl ester수율 47%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

2-[4-(Phenylsulfanyl)phenyl]-1-ethanol (1.22 g; 5.12 mmole), triphenylphosphine (2 g; 7.6 mmole) and 1,1′-(azodicarbonyl)dipiperidine were dissolved in dichloromethane (15 ml). After 10 minutes a solution of (S)-2-ethoxy-3-(4-hydroxyphenyl)propanoic acid (described in Example 40b) in dichloromethane (15 ml) was added and the reaction mixture was stirred over night at room temperature. The solid material was filtered off and the solvent evaporated. Chromatography of the residue on siliga gel using ethyl acetate:petroleum ether (40-60° C.), (1:99, 5:95 and 10:90) gave 1.24 g (yield 47%) of (S)-2-ethoxy-3-(4-{2-[4-(phenylsulfanyl)phenyl]ethoxy}phenyl)propanoic acid ethyl ester.

후처리

  1. filtrationThe solid material was filtered off
  2. customthe solvent evaporated

출처 및 근거

ORD 기록
ord-2622edb8072644899376e8580cfaa27d
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06630600B1

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