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Ethyl Acetate → (2R,5S)-2-Azidomethyl-5-(3-trifluoromethoxy-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester

HRID 1527349
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HRID 1527349 반응식
[CH2:1]([O:8][C:9]([N:11]1[C@H:15]([C:16](=[O:29])[NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]([F:28])([F:27])[F:26])[CH:19]=2)[CH2:14][CH2:13][C@@H:12]1[CH2:30]OS(C)(=O)=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:36]=[N+:37]=[N-:38].[Na+].CCOC(C)=O>CN(C=O)C.O>[CH2:1]([O:8][C:9]([N:11]1[C@H:15]([C:16](=[O:29])[NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]([F:28])([F:27])[F:26])[CH:19]=2)[CH2:14][CH2:13][C@@H:12]1[CH2:30][N:36]=[N+:37]=[N-:38])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 86673829(2R,5S)-2-Methanesulfonyloxymethyl-5-(3-trifluoromethoxy-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester

생성물 1

HCID 86673830(2R,5S)-2-Azidomethyl-5-(3-trifluoromethoxy-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester

시약·촉매·용매 2

HCID 962Water
용매
2회
HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

To a solution of (2R,5S)-2-methanesulfonyloxymethyl-5-(3-trifluoromethoxy-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester (589 mg, 1.14 mmol) in DMF (4.5 mL) was added a solution of sodium azide (371 mg, 5.7 mmol) in water (0.5 mL) and the mixture was stirred at 80° C. under nitrogen atmosphere overnight. EtOAc and a water were added, the layers were separated and the aqueous one back-extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The crude residue was purified by flash column chromatography on silica gel (c-hexane/EtOAc gradient 100:0 to 6:5) to give the desired compound. MS (LC-MS): 464 [MH−Boc]+; tR (HPLC conditions b) 5.73 min.

후처리

  1. customthe layers were separated
  2. extractionthe aqueous one back-extracted with EtOAc
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified by flash column chromatography on silica gel (c-hexane/EtOAc gradient 100:0 to 6:5)

출처 및 근거

ORD 기록
ord-86d8b1d516274f08a76080c739338619
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09085555B2

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