Acetyl chloride → 2-{[(Benzyloxy)carbonyl]amino}-2-methylpropyl acetate

HRID 372839Notes

Reaction equation

HRID 372839 reaction equation
[C:1]([NH:11][C:12]([CH3:16])([CH3:15])[CH2:13][OH:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[C:17](Cl)(=[O:19])[CH3:18].C(N(CC)CC)C>ClCCl>[C:17]([O:14][CH2:13][C:12]([NH:11][C:1]([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2])([CH3:16])[CH3:15])(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 12325553benzyl N-(1-hydroxy-2-methylpropan-2-yl)carbamate

Product 1

HCID 123255542-{[(Benzyloxy)carbonyl]amino}-2-methylpropyl acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane solution containing 2.52 g (0.011 mol) 2-carbobenzoxyamino-2-methyl-1-propanol and 1.17 g (0.015 mol) acetyl chloride was added dropwise with stirring 1.11 g (0.011 mol) triethylamine. The reaction was stirred at ambient temperature overnight and the dichloromethane was removed under reduced pressure. The triethylamine hydrochloride residue was triturated in anhydrous ether. Following filtration, the ether was removed under reduced pressure to afford 2.38 g (0.009 mol), 82%, crude 2-carbobenzoxyamino-2-methyl-1-propyl acetate as a pale yellow liquid, pmr (CDCl3) δ 7.2 (s, 5H), 5.4 (bs, 1H), 5.0 (s, 2H), 2.0 (s, 3H) and 1.2 (s, 6H) ppm.

Workup

  1. additionwas added dropwise
  2. customthe dichloromethane was removed under reduced pressure
  3. customThe triethylamine hydrochloride residue was triturated in anhydrous ether
  4. filtrationfiltration
  5. customthe ether was removed under reduced pressure

Sources & evidence

ORD record
ord-684958aeacef44e1b4984cf93c183f7a
Source dataset
uspto-grants-1978_05
Patent number
US04092420

Reaction notes

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