Hydrochloric Acid → Carbamic acid, (3-methyl-2-oxobutyl)-, 1,1-dimethylethyl ester (9CI)

HRID 1582653Notes

Reaction equation

HRID 1582653 reaction equation
CN(OC)[C:3](=[O:13])[CH2:4][NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[CH:16]([Mg]Cl)([CH3:18])[CH3:17].Cl>O1CCCC1.C(OCC)C>[C:9]([O:8][C:6]([NH:5][CH2:4][C:3](=[O:13])[CH:16]([CH3:18])[CH3:17])=[O:7])([CH3:10])([CH3:11])[CH3:12]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4428209tert-Butyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamateHCID 178418918HCID 178418918, compound

Product 1

HCID 22718430Carbamic acid, (3-methyl-2-oxobutyl)-, 1,1-dimethylethyl ester (9CI)

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
2.5 °C

Procedure

A solution of 10.9 g of N-tert.-butoxycarbonylglycine N-methyl-N-methoxyamide in 300 ml of anhydrous tetrahydrofuran and 100 ml of anhydrous diethyl ether was cooled at 0-5° C. while 100 ml of a 2M solution of isopropyl magnesium chloride in tetrahydrofuran was added slowly. The mixture was stirred at 0-5° C. for 4 h then poured into 1.5 liter of 1M hydrochloric acid. The product was extracted with three portions of 500 ml diethyl ether. Combined extracts were washed with 500 ml brine then dried over anhydrous magnesium sulphate, filtered and evaporated to give 8.38 g of 4-tert.-butoxycarbonylamino-2-methyl-3-butanone as a colourless oil which was used without further purification.

Workup

  1. additionwas added slowly
  2. extractionThe product was extracted with three portions of 500 ml diethyl ether
  3. washCombined extracts were washed with 500 ml brine
  4. dry with materialthen dried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-a619453196f548b0bd8d2c626b8e690d
Source dataset
uspto-grants-2004_05
Patent number
US06737429B2

Reaction notes

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