Ammonia → tert-Butyl (1-amino-2-methyl-1-oxopropan-2-yl)carbamate

HRID 927357Notes

Reaction equation

HRID 927357 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:14])([CH3:13])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.[N:30]1C=CC=CC=1.N>C(#N)C>[NH2:30][C:10](=[O:11])[C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 1049PyridineHCID 90495Di-tert-butyl dicarbonateHCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanine

Product 1

HCID 11287144tert-Butyl (1-amino-2-methyl-1-oxopropan-2-yl)carbamateYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-(tert-butoxycarbonylamino)-2-methylpropanoic acid (CAN: 30992-29-1, 20 g, 98 mmol), di-tert-butyl dicarbonate (CAN 24424-99-5, 27.67 g, 147 mmol) and pyridine (4.6 mL) in acetonitrile (500 mL) was stirred at room temperature for 20 min. Ammonia (10 mL) was added dropwise for 20 min. The resulting reaction mixture was stirred for 4 h. After removal of most of the solvent under reduced pressure, the solid was filtered off and washed with acetonitrile. The solid was brought to dryness under reduced pressure to give the title compound (17.5 g, 88%) as white solid; MS (EI): m/e 225.1 [M+Na]+.

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred for 4 h
  3. customAfter removal of most of the solvent under reduced pressure
  4. filtrationthe solid was filtered off
  5. washwashed with acetonitrile

Sources & evidence

ORD record
ord-0d5b7b40241c47a0a49d1b19104d3f92
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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