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

HRID 16343

反応式

HRID 16343 の反応式
[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]

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 8208851-Boc-D-Pyroglutamic acid ethyl esterHCID 178478191HCID 178478191、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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:

後処理

  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)

出典と根拠

ORDレコード
ord-bea5e79778174509a562f27c6f69c90b
出典データセット
uspto-grants-2010_06
特許番号
US07737141B2

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