Triethylamine → (S)-2-[3-(2-Benzenesulfonylphenyl)ureido]-3-(4-hydroxyphenyl) propionic acid methyl ester

HRID 852245노트

반응식

HRID 852245 반응식
[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:16]=[C:17]=[O:18])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:20][O:21][C:22](=[O:33])[C@H:23]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)[NH2:24].C(N(CC)CC)C>ClCCl>[CH3:20][O:21][C:22](=[O:33])[C@@H:23]([NH:24][C:17]([NH:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[S:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:8])=[O:9])=[O:18])[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 76956Methyl tyrosinate hydrochlorideHCID 212427352-Benzenesulfonylphenyl isocyanate

생성물 1

HCID 69374690(S)-2-[3-(2-Benzenesulfonylphenyl)ureido]-3-(4-hydroxyphenyl) propionic acid methyl ester수율 89%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

A solution of 2-benzenesulfonylphenyl isocyanate (600 mg, 2.31 mmol, prepared as described in Preparation 20) in dichloromethane (4 ml) was slowly added to a solution of L-tyrosine methyl ester hydrochloride (589 mg, 2.54 mmol) and triethylamine (0.64 ml, 4.62 mmol) in dichloromethane (4 ml) and the resulting reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane (50 ml) and washed with hydrochloric acid 1N (2×20 ml), saturated aqueous NaHCO3 (2×20 ml) and brine (1×20 ml). The organic layer was dried (MgSO4) and concentrated under reduced pressure to yield the title compound (930 mg, 89%) as a viscous oil.

후처리

  1. customthe resulting reaction mixture
  2. washwashed with hydrochloric acid 1N (2×20 ml), saturated aqueous NaHCO3 (2×20 ml) and brine (1×20 ml)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d0ffd3a0189547e1a1f4b4566e1d4d39
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253171B2

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