Tetrahydrofuran → ethyl (R)-2-tert-butoxycarbonylamino-5-(4-chlorophenyl)-5-oxopentanoate

HRID 16343

반응식

HRID 16343 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.O1CCCC1.[CH3:15][CH2:16][O:17][C:18]([C@H:20]1[CH2:24][CH2:23][C:22](=[O:25])[N:21]1[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[O:19]>O>[CH2:16]([O:17][C:18](=[O:19])[C@H:20]([NH:21][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][CH2:23][C:22]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:25])[CH3:15]

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 8208851-Boc-D-Pyroglutamic acid ethyl esterHCID 178478191HCID 178478191, 화합물

생성물 1

HCID 67371186ethyl (R)-2-tert-butoxycarbonylamino-5-(4-chlorophenyl)-5-oxopentanoate

시약·촉매·용매 1

HCID 962Water용매

실험 절차

4-Chlorophenyl magnesium bromide (1.0 M diethylether solution, 17.1 mL) was dropwise added to a tetrahydrofuran solution (100 mL) of (R)-5-oxopyrrolidin-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (CAS Register No. 128811-48-3, 4.0 g) over 20 min at −40° C. The resulting reaction solution was stirred while heating from −40° C. to 0° C. for 1 hr. To this solution, water was gradually added at 0° C. The reaction solution was extracted with ethyl acetate. The extract solution was washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane-ethyl acetate system) to give 5.6 g of the title compound as a colorless oily substance. The physical property values of this compound were as follows:

후처리

  1. customThe resulting reaction solution
  2. temperaturewhile heating from −40° C. to 0° C. for 1 hr
  3. extractionThe reaction solution was extracted with ethyl acetate
  4. washThe extract solution was washed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (heptane-ethyl acetate system)

출처 및 근거

ORD 기록
ord-bea5e79778174509a562f27c6f69c90b
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737141B2

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