2,4,6-Trimethylbenzoyl chloride → HCID 86681541, compound

HRID 2358898Notes

Reaction equation

HRID 2358898 reaction equation
[CH:1]1([N:7]([CH2:15][CH:16]([OH:18])[CH3:17])[C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:19][C:20]1[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[C:21]=1[C:22](Cl)=[O:23]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:19][C:20]1[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[C:21]=1[C:22]([O:18][CH:16]([CH3:17])[CH2:15][N:7]([C:8]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:14])[CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)=[O:23]

Participants

5

Reactant 2

HCID 970382,4,6-Trimethylbenzoyl chlorideHCID 86681542HCID 86681542, compound

Product 1

HCID 86681541HCID 86681541, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl cyclohexyl(2-hydroxypropyl)carbamate (1 g, 3.89 mmol) in dry toluene (10 ml), 2,4,6-trimethyl-benzoyl chloride (0.510 mL, 4.280 mmol) was added. The resultant reaction mixture was stirred at rt for 16 hours. The reaction mixture was diluted in ethyl acetate and washed with water and brine. The organic layer was dried over sodium sulphate, and concentrated to dryness to obtain 1-((tert-butoxycarbonyl)(cyclohexyl)amino)propan-2-yl 2,4,6-trimethylbenzoate. Yield: 1 g (64.10%); LCMS: m/z=404.4 [M+H], RT=2.76 min, (Column: Y, Program: P1)

Workup

  1. customThe resultant reaction mixture
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2c48b181bbf344fa9c375c6ba6d9d031
Source dataset
uspto-grants-2014_04
Patent number
US08685418B2

Reaction notes

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