Methanol → HCID 86701396, compound

HRID 870852Notes

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[S:23][CH:24]=[N:25][N:26]=1)C1C=CC=CC=1.CO>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[S:23][CH:24]=[N:25][N:26]=1

Participants

Conditions

Temperature: 0 °C

Procedure

BCl3 (1 M in CH2Cl2, 9.0 mL, 9.0 mmol) was added dropwise to a solution of (2S,5R)-6-(benzyloxy)-2-(1,3,4-thiadiazol-2-yl)-1,6-diaza-bicyclo[3.2.1]octan-7-one (560 mg, 1.8 mmol) in dry CH2Cl2 (20 mL) at −78° C. The mixture was stirred under a N2 atmosphere at 0° C. for 6 hrs., then, MeOH (9 mL) was slowly added dropwise at −78° C. The solvents were evaporated under vacuum at 0° C. to give (2S,5R)-6-hydroxy-2-(1,3,4-thiadiazol-2-yl)-1,6-diaza-bicyclo[3.2.1]octan-7-one (329 mg, 81%) as a yellow solid, which was used directly in the next step. ESI-MS (EI+, m/z): 227.1 [M+H]−.

Workup

customThe solvents were evaporated under vacuum at 0° C.

Sources & evidence

ORD record: ord-a9e5c256112444e9b98f891f1ad3f6eb
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969570B2

Reaction notes

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