Water → rel-(3S,5S)-3-(2-Bromoethyl)-7-chloro-5-cyclopropylethynyl-1,5-dihydro-5-(trifluoromethyl)-4,1-benzoxazepin-2(3H)-one

HRID 2296700Notes

Reaction equation

HRID 2296700 reaction equation
[Br:1][CH2:2][CH2:3][CH:4]1[O:10][C:9]([C:15]#[C:16][CH:17]2[CH2:19][CH2:18]2)([C:11]([F:14])([F:13])[F:12])[C:8]2[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:7]=2[N:6](CC2C=CC(OC)=CC=2)[C:5]1=[O:34].O>C(#N)C>[Br:1][CH2:2][CH2:3][C@@H:4]1[O:10][C@:9]([C:15]#[C:16][CH:17]2[CH2:18][CH2:19]2)([C:11]([F:13])([F:14])[F:12])[C:8]2[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:7]=2[NH:6][C:5]1=[O:34]

Participants

4

Reactant 2

HCID 962WaterHCID 183873763-(2-Bromoethyl)-7-chloro-5-cyclopropylethynyl-1,5-dihydro-1-(4-methoxybenzyl)-5-(trifluoromethyl)-4,1-benzoxazepin-2(3H)-one

Product 1

HCID 57189482rel-(3S,5S)-3-(2-Bromoethyl)-7-chloro-5-cyclopropylethynyl-1,5-dihydro-5-(trifluoromethyl)-4,1-benzoxazepin-2(3H)-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a room temperature solution of 1.13 g of 3-(2-bromoethyl)-7-chloro-5-cyclopropylethynyl-1,5-dihydro-1-(4-methoxybenzyl)-5-(trifluoromethyl)-4,1-benzoxazepin-2(3H)-one in 50 mL of acetonitrile was added 25 mL of water and 5.7 g of ceric ammonium nitrate. After 30 min, the reaction mixture was partitioned between water and ether, and the organic layer was washed with aqueous bicarbonate and brine, dried and evaporated. This produced two diastereomeric products which were separated by column chromatography over silica gel (elution with 10-25% ethyl acetate in hexanes). The first diastereomer eluted (270 mg) was the title compound.

Workup

  1. customthe reaction mixture was partitioned between water and ether
  2. washthe organic layer was washed with aqueous bicarbonate and brine
  3. customdried
  4. customevaporated
  5. customThis produced two diastereomeric products which
  6. customwere separated by column chromatography over silica gel (elution with 10-25% ethyl acetate in hexanes)
  7. washThe first diastereomer eluted (270 mg)

Sources & evidence

ORD record
ord-1e6ff7103a844e28b5531def43b1b0ae
Source dataset
uspto-grants-2002_12
Patent number
US06489320B1

Reaction notes

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