Tetrahydrofuran → benzyl N-(2-methyl-3-oxobutan-2-yl)carbamate

HRID 34743Notes

Reaction equation

HRID 34743 reaction equation
O.Cl.[NH2:3][C:4]([CH3:9])([CH3:8])[C:5](=[O:7])[CH3:6].C1COCC1.[OH-].[Na+].[CH2:17]([O:24][C:25](Cl)=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[CH2:17]([O:24][C:25]([NH:3][C:4]([CH3:9])([CH3:8])[C:5](=[O:7])[CH3:6])=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2×HCID 212986023-Amino-3-methyl-2-butanone hydrochloride hydrate

Product 1

HCID 21298536benzyl N-(2-methyl-3-oxobutan-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Amino-3-methyl-2-butanone hydrochloride hydrate [J. Org. Chem. 49, 1209 (1984)] (10.6 g., 0.076 mol was dissolved in 700 ml. 1:1 THF:H2O and the pH adjusted to 6.8 with dilute NaOH. Benzylchloroformate (11.93 ml., 0.084 ml.) was added dropwise, maintaining pH 6.8-7.0 by the simultaneous dropwise addition of dilute NaOH. The pH was so maintained until it stabilized. The reaction mixture was extracted 4×100 ml. CHCl3. The organic extracts were combined, filtered and stripped to yield title product as an oil, 9.26.

Workup

  1. dissolution, 0.076 mol was dissolved in 700 ml
  2. temperaturemaintaining pH 6.8-7.0
  3. temperatureThe pH was so maintained until it
  4. extractionThe reaction mixture was extracted 4×100 ml
  5. filtrationfiltered

Sources & evidence

ORD record
ord-38c2b1e4305046bb81a65d16186ff800
Source dataset
uspto-grants-1988_08
Patent number
US04762921

Reaction notes

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