Water → tert-butyl N-(2-methyl-1-oxopropan-2-yl)carbamate

HRID 1795999Notes

Reaction equation

HRID 1795999 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][C:8]([CH3:12])([CH3:11])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.O>CS(C)=O>[C:1]([O:5][C:6](=[O:13])[NH:7][C:8]([CH3:12])([CH3:11])[CH:9]=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 14578673tert-butyl N-(1-hydroxy-2-methylpropan-2-yl)carbamate

Product 1

HCID 14578674tert-butyl N-(2-methyl-1-oxopropan-2-yl)carbamateYield 71.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

(2-Hydroxy-1,1-dimethyl-ethyl)-carbamic acid tert-butyl ester (11.3 g, 0.06 mol) and triethylamine (18.2 g, 0.18 mol) in DMSO (180 mL) at 25° C. was treated with a solution of pyridine-sulfurtrioxide complex (28.6 g, 0.18 mol) in DMSO (150 mL). The resulting mixture was stirred for 0.5 h, poured into H2O (100 mL) and extracted with ether (3×100 mL). The organics were washed with 10% citric acid(aq) (250 mL), saturated NaHCO3 (250 mL) and then with brine (2×250 mL). The organics were dried and concentrated to an off-white solid which was recrystallized from hexanes to afford the desired material (8.0 g, 71%) as white needles: 13C NMR (DMSO-d6, 100 MHz) δ 202.07, 155.58, 78.95, 58.64, 28.42, 21.58.

Workup

  1. extractionextracted with ether (3×100 mL)
  2. washThe organics were washed with 10% citric acid(aq) (250 mL), saturated NaHCO3 (250 mL)
  3. customThe organics were dried
  4. concentrationconcentrated to an off-white solid which
  5. customwas recrystallized from hexanes

Sources & evidence

ORD record
ord-ed29f2d13c2544e590c0b23cbba1dc5b
Source dataset
uspto-grants-2006_04
Patent number
US07030118B2

Reaction notes

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