Boron Trichloride → HCID 86700678, compound

HRID 1406862Notes

Reaction equation

HRID 1406862 reaction equation
B(Cl)(Cl)Cl.[NH2:5][C:6]1[O:10][N:9]=[C:8]([C@@H:11]2[CH2:17][CH2:16][C@@H:15]3[CH2:18][N:12]2[C:13](=[O:27])[N:14]3[O:19]CC2C=CC=CC=2)[N:7]=1>C(Cl)Cl>[NH2:5][C:6]1[O:10][N:9]=[C:8]([C@@H:11]2[CH2:17][CH2:16][C@@H:15]3[CH2:18][N:12]2[C:13](=[O:27])[N:14]3[OH:19])[N:7]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 86700679HCID 86700679, compound

Product 1

HCID 86700678HCID 86700678, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

BCl3 (1M, 5.08 ml, 5.08 mmol) was added to a solution of (2S,5R)-2-(5-amino-1,2,4-oxadiazol-3-yl)-6-(benzyloxy)-1,6-diaza-bicyclo[3.2.1]octan-7-one (160 mg, 0.508 mmol) in dry DCM (8 mL) at −78° C. The mixture was stirred under N2 atmosphere at 0° C. for 2 hrs then, it was cooled to −78° C. and quenched with MeOH (1.0 mL). The solvent was removed by vacuum to afford (2S,5R)-2-(5-amino-1,2,4-oxadiazol-3-yl)-6-hydroxy-1,6-diaza-bicyclo[3.2.1]octan-7-one (110 mg) as a white solid, which was used directly in the next step. ESI-MS (EI+, m/z): 226 [M+H]+.

Workup

  1. temperatureit was cooled to −78° C.
  2. customquenched with MeOH (1.0 mL)
  3. customThe solvent was removed by vacuum

Sources & evidence

ORD record
ord-c8ab7d5e9609443396a40ffc8889cc4e
Source dataset
uspto-grants-2014_12
Patent number
US08916709B2

Reaction notes

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