Sodium borohydride → HCID 70390815, compound

HRID 621029Notes

Reaction equation

HRID 621029 reaction equation
[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]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 70390633HCID 70390633, compound

Product 1

HCID 70390815HCID 70390815, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0da8080390114a0b8c33eb51e30a07f1
Source dataset
uspto-grants-1989_04
Patent number
US04822790

Reaction notes

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