Acetyl chloride → HCID 178475031, compound

HRID 574842Notes

Reaction equation

HRID 574842 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1.C(N(CC)CC)C.[C:23](Cl)(=[O:25])[CH3:24]>ClCCl>[C:23]([NH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:4][CH2:3]1)(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178419079HCID 178419079, compound2×

Product 1

HCID 178475031HCID 178475031, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl (trans)-4-aminocyclohexylcarbamate (1.500 g) and triethylamine (2.93 mL, 2.125 g) were added to dichloromethane and stirred until the tert-butyl (trans)-4-aminocyclohexylcarbamate had dissolved completely. Acetyl chloride (0.577 g) was added slowly, and the solution was stirred at room temperature for 16 hours. The solvent was removed, and the residue taken up in ethyl acetate, washed with pH 4 buffer, washed with brine, dried with anhydrous sodium sulfate, and filtered. The filtrate was concentrated under vacuum.

Workup

  1. dissolutionhad dissolved completely
  2. customThe solvent was removed
  3. washwashed with pH 4 buffer
  4. washwashed with brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-bf0d3ebaff594fcb96eecdacbd29d6b4
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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