Acetyl chloride → Tert-butyl ((trans)-2-(4-acetamidophenyl)cyclopropyl)carbamate

HRID 529334Notes

Reaction equation

HRID 529334 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:10][C@H:9]2[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][CH:3]=1.[C:19](Cl)(=[O:21])[CH3:20]>ClCCl>[C:19]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:10][C@H:9]2[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[CH:4][CH:3]=1)(=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 86673140rac-tert-butyl N-[(1R,2S)-2-(4-aminophenyl)cyclopropyl]carbamate

Product 1

HCID 86708244Tert-butyl ((trans)-2-(4-acetamidophenyl)cyclopropyl)carbamateYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution of tert-butyl ((trans)-2-(4-aminophenyl)cyclopropyl)carbamate (1 g, 4.03 mmol) in dichloromethane (5 mL) was added TEA (0.842 mL, 6.04 mmol), acetyl chloride (0.315 mL, 4.43 mmol) and stirred for 2 h at RT. The reaction mixture was diluted with ice cold water (50 mL) and extracted with DCM (2×50 mL). The combined organic layer was dried over anhydrous sodium sulphate and concentrated. The residue was purified using silica gel (100-200 mesh) column chromatography, compound eluted in 2% MeOH in DCM to afford tert-butyl ((trans)-2-(4-acetamidophenyl)cyclopropyl)carbamate (900 mg, 77% yield) as brown solid. LCMS (ES) m/e 289.26 (M−H).

Workup

  1. extractionextracted with DCM (2×50 mL)
  2. dry with materialThe combined organic layer was dried over anhydrous sodium sulphate
  3. concentrationconcentrated
  4. customThe residue was purified
  5. washeluted in 2% MeOH in DCM

Sources & evidence

ORD record
ord-22406d1447064b6d80285ddfa212f841
Source dataset
uspto-grants-2016_05
Patent number
US09346840B2

Reaction notes

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