Ethyl isocyanate → HCID 59536904, compound

HRID 220653Notes

Reaction equation

HRID 220653 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.[CH2:22]([N:24]=[C:25]=[O:26])[CH3:23]>ClCCl>[CH2:22]([NH:24][C:25]([NH:1][CH2:2][CH:3]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1)=[O:26])[CH3:23]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 43094068tert-butyl N-{2-amino-1-[3-(trifluoromethyl)phenyl]ethyl}carbamate

Product 1

HCID 59536904HCID 59536904, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 500 mg (1.64 mmol) of the compound from Example 101A in 15 ml of dichloromethane was admixed at 0° C. with 260 μl (3.29 mmol) of ethyl isocyanate. The ice bath was removed and the reaction mixture was stirred for a further 1 h. Then all of the volatile constituents were removed on a rotary evaporator. The residue was purified by preparative HPLC [Method 23]. The product fraction was freed from the solvent on a rotary evaporator. Drying of the residue in an HV gave 546 mg (89% of theory) of the title compound.

Workup

  1. customThe ice bath was removed
  2. customThen all of the volatile constituents were removed on a rotary evaporator
  3. customThe residue was purified by preparative HPLC [Method 23]
  4. customThe product fraction was freed from the solvent on a rotary evaporator
  5. customDrying of the residue in an HV

Sources & evidence

ORD record
ord-a9d35ac1595e4879a5c57ee301390eac
Source dataset
uspto-grants-2012_06
Patent number
US08202895B2

Reaction notes

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