Triethylamine → tert-Butyl ethyl {1-[3-(trifluoromethyl)phenyl]ethane-1,2-diyl}biscarbamate

HRID 220652Notes

Reaction equation

HRID 220652 reaction equation
[NH2:1][CH2:2][CH:3]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1.C(N(CC)CC)C.Cl[C:30]([O:32][CH2:33][CH3:34])=[O:31]>ClCCl>[F:11][C:10]([F:13])([F:12])[C:6]1[CH:5]=[C:4]([CH:3]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19])[CH2:2][NH:1][C:30](=[O:31])[O:32][CH2:33][CH3:34])[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 43094068tert-butyl N-{2-amino-1-[3-(trifluoromethyl)phenyl]ethyl}carbamate

Product 1

HCID 59536750tert-Butyl ethyl {1-[3-(trifluoromethyl)phenyl]ethane-1,2-diyl}biscarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 500 mg (1.64 mmol) of the compound from Example 101A and 321 μl (2.30 mmol) of triethylamine in 15 ml of dichloromethane was cooled to 0° C. and admixed with 189 μl (1.97 mmol) of ethyl chloroformate. The ice bath was removed and the mixture was stirred for a further 1 h. The volatile constituents were removed on a rotary evaporator and the residue was purified by preparative HPLC [Method 20]. The product fractions were combined and freed from the solvents on a rotary evaporator. The residue was dried in an HV. This gave 527 mg (85% of theory) of the title compound.

Workup

  1. customThe ice bath was removed
  2. customThe volatile constituents were removed on a rotary evaporator
  3. customthe residue was purified by preparative HPLC [Method 20]
  4. customfreed from the solvents on a rotary evaporator
  5. customThe residue was dried in an HV

Sources & evidence

ORD record
ord-d218a10a4ddb4154846689ca4730f76a
Source dataset
uspto-grants-2012_06
Patent number
US08202895B2

Reaction notes

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