Triethylamine → benzyl (1S,3R)-3-(4-chlorobutanamido)cyclohexylcarbamate

HRID 526992

Reaction equation

HRID 526992 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][C@H:4]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:3]1.CCN(CC)CC.[Cl:26][CH2:27][CH2:28][CH2:29][C:30](Cl)=[O:31]>C(Cl)Cl>[Cl:26][CH2:27][CH2:28][CH2:29][C:30]([NH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][C@H:4]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:3]1)=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 783704-Chlorobutyryl chlorideHCID 69756715Benzyl ((1S,3R)-3-aminocyclohexyl)carbamate2×

Product 1

HCID 68101865benzyl (1S,3R)-3-(4-chlorobutanamido)cyclohexylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred slurry of benzyl N-[(1S,3R)-3-aminocyclohexyl]carbamate, 18e, (0.97 g, 3.41 mmol) in CH2Cl2 (34 mL), was added Et3N (1.00 mL, 7.15 mmol), followed by 4-chlorobutanoyl chloride (0.40 mL, 3.58 mmol). After stirring at room temperature, the mixture was diluted with CH2Cl2, washed with 1N HCl (2×), 1N NaOH (2×), and brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo to give 1.07 g of the desired product.

Workup

  1. washwashed with 1N HCl (2×), 1N NaOH (2×), and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-28144edabcba4971b3abc2245a2c7df5
Source dataset
uspto-grants-2016_05
Patent number
US09345708B2

Linked notes

Loading…