Boron tribromide → HCID 58468277, compound

HRID 2094640Notes

Reaction equation

HRID 2094640 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:29]2[CH:38]=[CH:37][C:36]3[C:31](=[CH:32][CH:33]=[C:34]([O:39]C)[CH:35]=3)[CH:30]=2)[C@@H:9]([C:13]2[CH:28]=[CH:27][C:16]([C:17]([NH:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:18])=[CH:15][CH:14]=2)[CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:29]2[CH:38]=[CH:37][C:36]3[C:31](=[CH:32][CH:33]=[C:34]([OH:39])[CH:35]=3)[CH:30]=2)[C@@H:9]([C:13]2[CH:28]=[CH:27][C:16]([C:17]([NH:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:18])=[CH:15][CH:14]=2)[CH2:10][CH2:11][CH3:12])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67438208HCID 67438208, compound

Product 1

HCID 58468277HCID 58468277, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl N-(4-{(1S)-1-[(4-chlorophenyl)(6-methoxy-2-naphthyl)methyl]butyl}benzoyl)-β-alaninate (EXAMPLE 2, Step A, 300 mg, 0.538 mmol) in DCM (10 mL) at 0° C. was slowly added BBr3 (1.0 M in DCM, 2.69 mL, 2.69 mmol). The resulting mixture was allowed to warm to room temperature and stirred for 6 hours. After diluting with DCM, the mixture was washed with water, then saturated NaCl (aq). The organic layer was dried over MgSO4, filtered, then concentrated to afford the title product. LC2 2.65 min. [M+H]+ 544.

Workup

  1. customat 0° C.
  2. washthe mixture was washed with water
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7e9737ddc18144e08473b5e7f1512131
Source dataset
uspto-grants-2013_05
Patent number
US08445538B2

Reaction notes

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