Acetonitrile → HCID 86671129, compound

HRID 2402790Notes

Reaction equation

HRID 2402790 reaction equation
[NH2:1][CH2:2][CH:3]([NH:14]C(=O)OC(C)(C)C)[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)[CH:26]([CH3:28])[CH3:27])(C)C.Cl[C:32]([O:34][CH2:35][CH2:36][Br:37])=[O:33].[C:38](=[O:41])([O-])[OH:39].[Na+].[C:43](#N)C>C(OCC)(=O)C>[F:13][C:10]([F:11])([F:12])[C:6]1[CH:5]=[C:4]([CH:3]([NH:14][C:32](=[O:33])[O:34][CH2:35][CH2:36][Br:37])[CH2:2][NH:1][C:38](=[O:41])[O:39][C:26]([CH3:28])([CH3:43])[CH3:27])[CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 5

HCID 6342Acetonitrile2×HCID 785282-Bromoethyl chloroformateHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 43094068tert-butyl N-{2-amino-1-[3-(trifluoromethyl)phenyl]ethyl}carbamate

Product 1

HCID 86671129HCID 86671129, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 272 mg (0.89 mmol) of the compound from Example 101A and 171 μl (0.98 mmol) of N,N-diisopropylethylamine in 3 ml of acetonitrile was admixed dropwise with a solution of 106 μl (0.98 mmol) of 2-bromoethyl chloroformate in 2 ml of acetonitrile. For work-up, after 10 minutes, ethyl acetate and saturated aqueous sodium hydrogen carbonate solution were added. The organic phase was separated, washed again with saturated aqueous sodium hydrogen carbonate solution, dried over sodium sulphate and freed from the volatile constituents on a rotary evaporator. Drying of the residue in an HV gave 352 mg (82% of theory) of the title compound.

Workup

  1. customThe organic phase was separated
  2. washwashed again with saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over sodium sulphate
  4. customfreed from the volatile constituents on a rotary evaporator
  5. customDrying of the residue in an HV

Sources & evidence

ORD record
ord-d170fe8e4d194d88acebdd4551a4dbbb
Source dataset
uspto-grants-2014_08
Patent number
US08796324B2

Reaction notes

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