Boron Trichloride → HCID 86701376, compound

HRID 515599Notes

Reaction equation

HRID 515599 reaction equation
B(Cl)(Cl)Cl.C([O:12][N:13]1[C:19](=[O:20])[N:18]2[CH2:21][C@H:14]1[CH2:15][CH2:16][C@H:17]2[C:22]1[CH:26]=[C:25]([C:27]#[N:28])[O:24][N:23]=1)C1C=CC=CC=1>C(Cl)Cl>[OH:12][N:13]1[C:19](=[O:20])[N:18]2[CH2:21][C@H:14]1[CH2:15][CH2:16][C@H:17]2[C:22]1[CH:26]=[C:25]([C:27]#[N:28])[O:24][N:23]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 86701374HCID 86701374, compound

Product 1

HCID 86701376HCID 86701376, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

BCl3 (1M in DCM, 1.6 mL) was added to a solution of 3-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octan-2-yl)isoxazole-5-carbonitrile (104 mg, 0.32 mmol) in dry CH2Cl2 (9 mL) at −78° C. The mixture was stirred −78° C. for 2 hrs and quenched carefully with MeOH (2 mL). The solvents were removed in vacuum and the residue was partitioned between EtOAc and water. The organic phase was separated, washed with brine, dried over Na2SO4, and concentrated to afford 3-((2S,5R)-6-hydroxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octan-2-yl)isoxazole-5-carbonitrile (45 mg, 60%), which was used directly in the next step. ESI-MS (EI+, m/z): 235.1 [M+H]+.

Workup

  1. customquenched carefully with MeOH (2 mL)
  2. customThe solvents were removed in vacuum
  3. customthe residue was partitioned between EtOAc and water
  4. customThe organic phase was separated
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b5b966729b804809ac8e9fff1530d275
Source dataset
uspto-grants-2015_08
Patent number
US09108966B2

Reaction notes

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