Acetic Acid → HCID 70447662, compound

HRID 127898Notes

Reaction equation

HRID 127898 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) of 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 drop-wise 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-d0a2efcec4094a329951f6b90cbecd3a
Source dataset
uspto-grants-1981_03
Patent number
US04257947

Reaction notes

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