Boron tribromide → HCID 69772095, compound

HRID 1858975Notes

Reaction equation

HRID 1858975 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([S:21]([NH:24][C@@H:25]([CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:26]([OH:28])=[O:27])(=[O:23])=[O:22])=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)[Br:37]>ClCCl.O>[BrH:37].[OH:2][C:3]1[CH:4]=[C:5]([N:9]2[CH2:10][CH2:11][N:12]([C:15]3[CH:16]=[CH:17][C:18]([S:21]([NH:24][C@@H:25]([CH2:29][C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[C:26]([OH:28])=[O:27])(=[O:22])=[O:23])=[CH:19][CH:20]=3)[CH2:13][CH2:14]2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 12114676HCID 12114676, compound

Product 1

HCID 69772095HCID 69772095, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a stirred suspension of (S)-2-{4-[4-(3-methoxy-phenyl)-piperazin-1-yl]-benzenesulfonylamino}-3-phenyl-propionic acid (0.103 g, 0.000208 mol) in dichloro-methane (2 mL) at -78° C. under nitrogen was added dropwise a 1.0 M solution of boron tribromide in dichloromethane (1.0 mL, 0.0010 mol). The mixture was stirred for 15 minutes at -78° C. and then allowed to warm to +3° C. After 6 hours, the reaction mixture was diluted with water. The resulting suspension was stirred overnight. The solids were filtered off, washed with additional water, and dried in vacuo to give the title compound as an off-white solid; yield 0.069 g (69%), mp=229-230° C.

Workup

  1. temperatureto warm to +3° C
  2. waitAfter 6 hours
  3. stirringThe resulting suspension was stirred overnight
  4. filtrationThe solids were filtered off
  5. washwashed with additional water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-f2b2f6cac43d4585a202213008c894df
Source dataset
uspto-grants-2000_11
Patent number
US06153612

Reaction notes

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