Water → HCID 54139749, compound

HRID 1457987Notes

Reaction equation

HRID 1457987 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:13](=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].O>C(O)C>[C:1]([O:5][C:6]([NH:8][C:9]1([CH:13]([OH:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 53817402HCID 53817402, compound

Product 1

HCID 54139749HCID 54139749, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 70.21 g (257 mmol) portion of ethyl 1-tert-butoxycarbonylamino-β-oxocyclobutanepropanoate was dissolved in 500.0 ml of ethanol. Thereto was added 4.86 g (514 mmol) of sodium borohydride in small portions under ice cooling. After 2 hours of stirring at the same temperature, water was added and the solvent was evaporated. The resulting residue was extracted with chloroform, washed with saturated brine and then dried over anhydrous sodium sulfate. By evaporating the solvent, 65.25 g (93%) of the title compound was obtained.

Workup

  1. additionwas added
  2. customthe solvent was evaporated
  3. extractionThe resulting residue was extracted with chloroform
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customBy evaporating the solvent

Sources & evidence

ORD record
ord-b2bf7aff4ead4f5e8b89c9b3c3c92d7a
Source dataset
uspto-grants-1998_12
Patent number
US05849757

Reaction notes

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