(4-Bromophenyl)(phenyl)methyl 2,2,2 trichloroethanimidoate → HCID 10047452, compound

HRID 1180445Notes

Reaction equation

HRID 1180445 reaction equation
[C:1]([CH2:3][NH:4][C:5](=[O:12])[C@@H:6]([OH:11])[CH2:7][CH:8]([CH3:10])[CH3:9])#[N:2].ClC(Cl)(Cl)C(=N)O[CH:17]([C:24]1[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>ClCCCl>[Br:30][C:27]1[CH:26]=[CH:25][C:24]([CH:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[O:11][C@@H:6]([CH2:7][CH:8]([CH3:9])[CH3:10])[C:5]([NH:4][CH2:3][C:1]#[N:2])=[O:12])=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 69473260(4-Bromophenyl)(phenyl)methyl 2,2,2 trichloroethanimidoate2×HCID 86605382HCID 86605382, compound

Product 1

HCID 10047452HCID 10047452, compoundYield 626.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

(2S)-N-(cyanomethyl)-2-hydroxy-4-methylpentanamide from example 67 step 1 (22.5 g, 0.132 mol) and (1R)-(-1-10-camphorsulfonic acid (2.85 g, 0.012 mol, 0.1 eg) were added to 1,2-dichloroethane (135 mL) and the suspension was heated to 50° C. (4-bromophenyl)(phenyl)methyl 2,2,2-trichloroethanimidoate (50 g, 0.123 mol, 0.93 eg) was added portionwise over 15 min. then reaction mixture was stirred at 50° C. for 10 min. The reaction was repeated with 2×50 g and 1×69 g of (4-bromophenyl)(phenyl)methyl 2,2,2 trichloroethanimidoate, using same proportions of other reagents. All the batches were combined and evaporated to give a dark red oil (320 g). The latter was dissolved in toluene (600 mL); insoluble material was filtered off and the filtrate was charged on a chromatography column, eluted with 5% EtOAc/toluene to give the title compound.

Workup

  1. additionwas added portionwise over 15 min.
  2. customreaction mixture
  3. customevaporated

Sources & evidence

ORD record
ord-2c2784a9cd4542d4997e4243ebeb82ff
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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