Methyl chloroformate → tert-Butyl methyl {1-[3-(trifluoromethyl)phenyl]ethane-1,2-diyl}biscarbamate

HRID 220651Notes

Reaction equation

HRID 220651 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][CH3:33])=[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][CH3:33])[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 43094068tert-butyl N-{2-amino-1-[3-(trifluoromethyl)phenyl]ethyl}carbamate

Product 1

HCID 59536898tert-Butyl methyl {1-[3-(trifluoromethyl)phenyl]ethane-1,2-diyl}biscarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Of the compound from Example 101A, 500 mg (1.64 mmol) were introduced in dichloromethane together with 320 μl (2.30 mmol) of triethylamine, with ice cooling, and 152 μl (1.97 mmol) of methyl chloroformate were added. The ice bath was removed and the mixture was stirred for a further 1 h. The solvent was 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, and the residue was dried in an HV. This gave 428 mg (72% of theory) of the title compound.

Workup

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

Sources & evidence

ORD record
ord-26999dc97a75425ab8deb3e8b4d45598
Source dataset
uspto-grants-2012_06
Patent number
US08202895B2

Reaction notes

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