Triethylamine → HCID 178453922, compound

HRID 1984932Notes

Reaction equation

HRID 1984932 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]1[CH2:13][CH2:12][C@@H:11]([CH2:14][CH2:15][NH2:16])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]1[CH2:9][CH2:10][C@@H:11]([CH2:14][CH2:15][NH:16][C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 178453918HCID 178453918, compound

Product 1

HCID 178453922HCID 178453922, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of cis-[4-(2-amino-ethyl)-cyclohexyl]-carbamic acid tert-butyl ester (4.84 g, 20 mmol) in CH2Cl2 (50 mL) and triethylamine (3.06 mL, 22 mmol) was added benzyl chloroformate (3.13 mL, 22 mmol) and the mixture was stirred for 4 hr. The resulting mixture was washed with water, 1 M aqueous HCl, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography (silica gel, CH2Cl2 to 10% MeOH in CH2Cl2) to give cis-[4-(2-benzyloxycarbonylamino-ethyl)-cyclohexyl]-carbamic acid tert-butyl ester (5.46 g, 73%) as a colorless oil.

Workup

  1. washThe resulting mixture was washed with water, 1 M aqueous HCl
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (silica gel, CH2Cl2 to 10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-c43dd89686604829ae6027c6d7efb341
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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