Boron Trichloride → HCID 86700687, compound

HRID 1406869Notes

Reaction equation

HRID 1406869 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[O:26][N:25]=[CH: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[O:26][N:25]=[CH:24][N:23]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 86700686HCID 86700686, compound

Product 1

HCID 86700687HCID 86700687, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

BCl3 (1M in DCM, 1.2 mL, 1.2 mmol) was added to (2S,5R)-6-(benzyloxy)-2-(1,2,4-oxadiazol-5-yl)-1,6-diaza-bicyclo[3.2.1]octan-7-one (50 mg, 0.167 mmol) in DCM (10 mL) at −78° C. The mixture was warmed to 0° C. and stirred for 2 hrs. The reaction was then quenched by the addition of MeOH (1 mL) and the resulting solution was concentrated under vacuum to give (2S,5R)-6-hydroxy-2-(1,2,4-oxadiazol-5-yl)-1,6-diaza-bicyclo[3.2.1]octan-7-one (34 mg, 98%) as a white solid, which was used directly in the next step. ESI-MS (EI+, 211, m/z): [M+H]+.

Workup

  1. customThe reaction was then quenched by the addition of MeOH (1 mL)
  2. concentrationthe resulting solution was concentrated under vacuum

Sources & evidence

ORD record
ord-2aebe0fee75c4d62b52c37cebbfe74d4
Source dataset
uspto-grants-2014_12
Patent number
US08916709B2

Reaction notes

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