Sodium borohydride → HCID 70390815, 화합물

HRID 621121노트

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HRID 621121 반응식
[BH4-].[Na+].C[O:4][C:5]([C@H:7]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=2[O:20][CH3:21])[C:9](=[O:22])[C@H:8]1[NH:23][C:24](=[O:32])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=O>O1CCCC1>[CH3:21][O:20][C:13]1[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:12]=1[CH2:11][N:10]1[C@H:7]([CH2:5][OH:4])[C@H:8]([NH:23][C:24](=[O:32])[CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:9]1=[O:22]

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 70390633HCID 70390633, 화합물

생성물 1

HCID 70390815HCID 70390815, 화합물수율 91.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Under ice-cooling and stirring, 12 ml of an aqueous solution containing 570 mg of sodium borohydride is added to a solution of 2.06 g of cis-1-(2,4-dimethoxybenzyl)-3-phenylacetamido-2-oxoazetidine-4-carboxylic acid methyl ester in 24 ml of tetrahydrofuran. The reaction mixture is stirred for 30 minutes under ice-cooling and then for 1.5 hours at room temperature. The tetrahydrofuran is distilled off in vacuo and an aqueous sodium chloride solution and ethyl acetate are added to the residue. The resulting ethyl acetate layer is separated and washed successively with an aqueous sodium hydrogen carbonate and an aqueous sodium chloride. It is then dried over magnesium sulfate and the solvent is distilled off in vacuo. Ether is added to the residue and the precipitated crystals are collected by filtration to give 1.75 g (91%) of cis-1-(2,4-dimethoxybenzyl)-4-hydroxymethyl-3-phenylacetamido-2-oxoazetidine, m.p. 152°-154° C.

후처리

  1. temperatureUnder ice-cooling
  2. stirringThe reaction mixture is stirred for 30 minutes under ice-
  3. temperaturecooling
  4. distillationThe tetrahydrofuran is distilled off in vacuo
  5. additionan aqueous sodium chloride solution and ethyl acetate are added to the residue
  6. customThe resulting ethyl acetate layer is separated
  7. washwashed successively with an aqueous sodium hydrogen carbonate
  8. dry with materialIt is then dried over magnesium sulfate
  9. distillationthe solvent is distilled off in vacuo
  10. additionEther is added to the residue
  11. filtrationthe precipitated crystals are collected by filtration

출처 및 근거

ORD 기록
ord-89dcbb9b08a142fabfb1210880eb5c3e
출처 데이터셋
uspto-grants-1989_04
특허 번호
US04822788

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