Acetic Anhydride → Tert-butyl 2-acetamido-1-(4-chlorophenyl)ethylcarbamate

HRID 423094Notes

Reaction equation

HRID 423094 reaction equation
[NH2:1][CH2:2][CH:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1.C(N(C(C)C)C(C)C)C.[C:28](OC(=O)C)(=[O:30])[CH3:29]>C1COCC1>[C:28]([NH:1][CH2:2][CH:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])[C:4]1[CH:5]=[CH:6][C:7]([Cl:10])=[CH:8][CH:9]=1)(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 57750386tert-butyl N-[2-amino-1-(4-chlorophenyl)ethyl]carbamate2×

Product 1

HCID 57750416Tert-butyl 2-acetamido-1-(4-chlorophenyl)ethylcarbamateYield 62.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl 2-amino-1-(4-chlorophenyl)ethylcarbamate (Intermediate 73) (0.208 g, 0.77 mmol) and N-ethyldiisopropylamine (0.266 mL, 1.54 mmol) in THF (5 mL) was treated with acetic anhydride (0.102 mL, 1.08 mmol). The resulting solution was stirred at ambient temperature for 2 hours. The mixture was partitioned between DCM and sodium bicarbonate solution. The organic layer was concentrated and the residue was purified by flash column chromatography on silica using gradient elution (10% ethyl acetate/DCM to 40% ethyl acetate/DCM). The desired product, tert-butyl 2-acetamido-1-(4-chlorophenyl)ethylcarbamate (0.151 g, 62.7%), was thus isolated as a colourless solid.

Workup

  1. customThe mixture was partitioned between DCM and sodium bicarbonate solution
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified by flash column chromatography on silica using gradient elution (10% ethyl acetate/DCM to 40% ethyl acetate/DCM)

Sources & evidence

ORD record
ord-68bdbc6c635d484f94df78bc9ed2ddb4
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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