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Hydrochloric Acid → 2-Ethoxy-3-(2,2,2-trifluoro-acetylamino)-pyrrolidine-1-carboxylic acid benzyl ester

HRID 1976548
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HRID 1976548 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH:13]([NH:16][C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[C:12]1=[O:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].Cl.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+].[CH2:37](O)[CH3:38]>O1CCOCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH:13]([NH:16][C:17](=[O:22])[C:18]([F:21])([F:19])[F:20])[CH:12]1[O:23][CH2:37][CH3:38])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 6

HCID 313Hydrochloric Acid2회HCID 702EthanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride2회HCID 107114652-Oxo-3-(2,2,2-trifluoro-acetylamino)-pyrrolidine-1-carboxylic acid benzyl ester

생성물 1

HCID 54116192
2-Ethoxy-3-(2,2,2-trifluoro-acetylamino)-pyrrolidine-1-carboxylic acid benzyl ester

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

실험 절차

To Intermediate 4 (34 g) in ethanol (1070 ml) at −5° C. was added sodium borohydride (9.86 g). A solution of 4M hydrogen chloride in 1,4-dioxan (20 ml) was then added dropwise. Periodically further portions of 4M hydrogen chloride in 1,4-dioxan (2×5 ml, 1×10 ml) and sodium borohydride (2 g) were added. After 3 h, concentrated sulphuric acid (11 ml) was added and the mixture warmed to room temperature for 2 h. Saturated aqueous sodium bicarbonate (300 ml) was then added and the ethanol and dioxan removed in vacuo. The residue was diluted with water (500 ml) and extracted with ethyl acetate (3×500 ml). The combined extracts were washed with brine and dried (MgSO4). The solvent was removed in vacuo and the residue purified by flash chromatography on silica gel 9385 eluting with ether, to give the title compound (21 g). Mass spec. MNH4+ (found) 378 MNH4+ (calculated) 378

후처리

  1. customthe ethanol and dioxan removed in vacuo
  2. additionThe residue was diluted with water (500 ml)
  3. extractionextracted with ethyl acetate (3×500 ml)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo
  7. customthe residue purified by flash chromatography on silica gel 9385 eluting with ether

출처 및 근거

ORD 기록
ord-e6574531a0d24c5a8f58e16e3fbf49e0
출처 데이터셋
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06228853B1

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