Boron Trichloride → HCID 86700676, compound

HRID 1406861Notes

Reaction equation

HRID 1406861 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[N:26]=[CH:25][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[N:26]=[CH:25][O:24][N:23]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 86700677HCID 86700677, compound

Product 1

HCID 86700676HCID 86700676, compoundYield 127.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

BCl3 (1M, 3.34 mL, 3.33 mmol) was added to a solution of (2S,5R)-6-(benzyloxy)-2-(1,2,4-oxadiazol-3-yl)-1,6-diaza-bicyclo[3.2.1]octan-7-one (200 mg, 0.67 mmol) in dry DCM (45 mL) at −78° C. The mixture was stirred at 0° C. for 2 hrs., then it was cooled to −78° C. and quenched with MeOH (8 mL). The solvent was removed by vacuum to give (2S,5R)-6-hydroxy-2-(1,2,4-oxadiazol-3-yl)-1,6-diaza-bicyclo[3.2.1]octan-7-one (180 mg) as a white solid, which was used directly in the next step. ESI-MS (EI+, m/z): 209 [M−H]+.

Workup

  1. temperature, then it was cooled to −78° C.
  2. customquenched with MeOH (8 mL)
  3. customThe solvent was removed by vacuum

Sources & evidence

ORD record
ord-f37df13282d94915a2be8742cc7b0d5a
Source dataset
uspto-grants-2014_12
Patent number
US08916709B2

Reaction notes

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