Acetic Acid → HCID 70447662, compound

HRID 616160Notes

Reaction equation

HRID 616160 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[C:12](=[O:13])[NH:11][CH:10]1[C:14](OC)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].C(O)(=O)C.[BH4-]>O1CCCC1.O>[C:1]([O:5][C:6]([NH:8][C@H:9]1[C:12](=[O:13])[NH:11][C@H:10]1[CH2:14][OH:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 28123BorohydrideHCID 4311764Sodium borohydrideHCID 12762152Methyl 3-t-butoxycarbonylamino-4-oxoazetidine-2-carboxylate

Product 1

HCID 70447662HCID 70447662, compoundYield 50.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.0 g (8.2 mmole) of methyl 3-t-butoxycarbonylamino-4-oxoazetidine-2-carboxylate in 20 ml of tetrahydrofuran is cooled in ice and a solution of 0.75 g (20 mmole) sodium borohydride in 10 ml of water is added. The mixture is stirred 20 min at 0° and then 1.5 hr at room temperature. Acetic acid is added dropwise to decompose the excess borohydride and the mixture is concentrated in vacuum. The residue is diluted with brine and extracted with ethyl acetate. The organic phase is washed with brine and 5% NaHCO3 ; dried over magnesium sulfate and evaporated to dryness to give 0.9 g (50%) of the title product as white crystals, mp 128°-131°.

Workup

  1. custom1.5 hr
  2. customat room temperature
  3. concentrationthe mixture is concentrated in vacuum
  4. additionThe residue is diluted with brine
  5. extractionextracted with ethyl acetate
  6. washThe organic phase is washed with brine and 5% NaHCO3
  7. dry with materialdried over magnesium sulfate
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-6d6b6bfc71e44fb499d3984258d48391
Source dataset
uspto-grants-1978_02
Patent number
US04072674

Reaction notes

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