Boron Trichloride → HCID 86700690, compound

HRID 1406871Notes

Reaction equation

HRID 1406871 reaction equation
B(Cl)(Cl)Cl.[NH2:5][C:6]1[N:10]=[C:9]([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)[O:8][N:7]=1>C(Cl)Cl>[NH2:5][C:6]1[N:10]=[C:9]([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])[O:8][N:7]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 86700688HCID 86700688, compound

Product 1

HCID 86700690HCID 86700690, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

BCl3 (1M, 15.87 mL, 15.87 mmol) was added to a solution of (2S,5R)-2-(3-amino-1,2,4-oxadiazol-5-yl)-6-(benzyloxy)-1,6-diaza-bicyclo[3.2.1]octan-7-one (1.0 g, 3.17 mmol) in dried DCM (20 mL) at −78° C. The mixture was stirred under N2 atmosphere at 0° C. for 2 hrs, cooled to −78° C. and quenched with MeOH (2 mL). The solvent was removed under vacuum to give ((2S,5R)-2-(3-amino-1,2,4-oxadiazol-5-yl)-6-hydroxy-1,6-diaza-bicyclo[3.2.1]octan-7-one (700 mg), which was used in the next step directly. ESI-MS (EI+, m/z): 226 [M+H]+.

Workup

  1. temperaturecooled to −78° C.
  2. customquenched with MeOH (2 mL)
  3. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-bdbc193e0c6e4d2e97404262973b1353
Source dataset
uspto-grants-2014_12
Patent number
US08916709B2

Reaction notes

Loading…