1,2-Dichloroethane → Ethyl 3-((R)-1-benzyl-5-oxopyrrolidine-2-carboxamido)-2-hydroxy-4-phenylbutanoate

HRID 1474134노트

반응식

HRID 1474134 반응식
[CH2:1]([N:8]1[C:12](=[O:13])[CH2:11][CH2:10][C@@H:9]1[C:14]([OH:16])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.[NH2:27][CH:28]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH:29]([OH:35])[C:30]([O:32][CH2:33][CH3:34])=[O:31].C(Cl)CCl.CCN(C(C)C)C(C)C>C1COCC1.CN(C=O)C>[CH2:1]([N:8]1[C:12](=[O:13])[CH2:11][CH2:10][C@@H:9]1[C:14]([NH:27][CH:28]([CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[CH:29]([OH:35])[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

8

반응물 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 18690978Ethyl 3-amino-2-hydroxy-4-phenylbutanoateHCID 23390401HCID 23390401, 화합물

생성물 1

HCID 66644659Ethyl 3-((R)-1-benzyl-5-oxopyrrolidine-2-carboxamido)-2-hydroxy-4-phenylbutanoate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (R)-1-benzyl-5-oxopyrrolidine-2-carboxylic acid (2440 mg, 11.13 mmol) in a mixture of 24 ml THF and 4 ml DMF were successively added at 5° C. 1-hydroxybenzotriazole (1875 mg, 12.24 mmol), ethyl 3-amino-2-hydroxy-4-phenylbutanoate (2485 mg, 11.13 mmol; preparation described in WO 98/25883, example 8a on page 24), EDC (2347 mg, 12.24 mmol) and DIPEA (6.41 mL; 4750 mg, 36.7 mmol). After stirring overnight at room temperature the reaction mixture was concentrated under reduced pressure, water was added and the obtained mixture was extracted three times with ethyl acetate. The organic layer was washed successively with aq. saturated NaHCO3 (2×), 10% aq. citric acid solution (3×) and brine, dried over Na2SO4 and the solvent was then removed under reduced pressure. The title compound was obtained as a yellow oil (4550 mg, yield: 96%), which was used without further purification in the next step.

후처리

  1. additionwere successively added at 5° C
  2. concentrationwas concentrated under reduced pressure, water
  3. additionwas added
  4. extractionthe obtained mixture was extracted three times with ethyl acetate
  5. washThe organic layer was washed successively with aq. saturated NaHCO3 (2×), 10% aq. citric acid solution (3×) and brine
  6. dry with materialdried over Na2SO4
  7. customthe solvent was then removed under reduced pressure

출처 및 근거

ORD 기록
ord-cfba05512fde449fb7beee55097a7138
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018206B2

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