Acetic Acid → HCID 70417750, compound

HRID 414862Notes

Reaction equation

HRID 414862 reaction equation
[CH2:1]([O:8][N:9]1[C@@H:12]([C:13](OC)=[O:14])[C@H:11]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:10]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].C(O)(=O)C.[Cl-].[Na+]>O1CCCC1.O.C(OCC)(=O)C>[CH2:1]([O:8][N:9]1[C@@H:12]([CH2:13][OH:14])[C@H:11]([NH:17][C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[C:10]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 5234Sodium ChlorideHCID 4311764Sodium borohydride2×HCID 70418462HCID 70418462, compound

Product 1

HCID 70417750HCID 70417750, compoundYield 24.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-15 °C

Procedure

In 60 ml of tetrahydrofuran is dissolved 5.95 g (17 mmole) of trans-1-benzyloxy-3-(tert-butoxycarbonylamino)-4-methoxycarbonyl-2-azetidinone obtained in the same manner as the method described in The Journal of Organic Chemistry, 48 (1983), 3556-3559, and a solution of 965 mg (25.5 mmole) of sodium borohydride in 15 ml of water is added dropwise to the solution under cooling at -15° C. with stirring over the period of 10 minutes. After the addition is completed, the reaction solution is stirred at -5° to -10° C. for 40 minutes, and acetic acid is added to decompose excess sodium borohydride. 100 ml of ethyl acetate and 30 ml of aqueous sodium chloride solution are added, and the mixture is shaken, followed by separation of the ethyl acetate layer. The aqueous layer is extracted again with ethyl acetae, and the ethyl acetate layer are combined, washed with saturated aqueous sodium hydrogen carbonate solution and aqueous sodium chloride solution successively, and dried over anhydrous megnesium sulfate. The solvent is distilled off under reduced pressure, and the residue i purified by column chromatography (silica gel, 250 g; n-hexabe-ethyl acetate =3:2, then 1:1). The fractions containing the objective compound are collected, and the solvent is distilled off under reduced pressure. Ether and petroleum ether (1:2) are added to the residue, and the resulting crystals are recovered by filtration to give 1.33 g (24.3%) of trans-1-benzyloxy-3-(tert-butoxycarbonylamino)-4-hydroxymethyl-2-azetidinone.

Workup

  1. customobtained in the same manner as the method
  2. additionAfter the addition
  3. stirringthe reaction solution is stirred at -5° to -10° C. for 40 minutes
  4. stirringthe mixture is shaken
  5. customfollowed by separation of the ethyl acetate layer
  6. extractionThe aqueous layer is extracted again with ethyl acetae
  7. washwashed with saturated aqueous sodium hydrogen carbonate solution and aqueous sodium chloride solution successively
  8. dry with materialdried over anhydrous megnesium sulfate
  9. distillationThe solvent is distilled off under reduced pressure
  10. customthe residue i purified by column chromatography (silica gel, 250 g
  11. additionThe fractions containing the objective compound
  12. customare collected
  13. distillationthe solvent is distilled off under reduced pressure
  14. additionEther and petroleum ether (1:2) are added to the residue
  15. filtrationthe resulting crystals are recovered by filtration

Sources & evidence

ORD record
ord-e63ed74fc0ed4928b33df0f3720bd526
Source dataset
uspto-grants-1988_12
Patent number
US04794108

Reaction notes

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