HCID 86701403, compound → HCID 86701404, compound

HRID 870860Notes

Reaction equation

HRID 870860 reaction equation
C([O:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[CH2:11][CH2:12][C@H:13]2[C:18]1[S:22][C:21]([N:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]2)=[N:20][N:19]=1)C1C=CC=CC=1>C1COCC1.[OH-].[OH-].[Pd+2]>[OH:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[CH2:11][CH2:12][C@H:13]2[C:18]1[S:22][C:21]([N:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]2)=[N:20][N:19]=1

Participants

4

Reactant 1

HCID 86701403HCID 86701403, compound

Product 1

HCID 86701404HCID 86701404, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of tert-butyl 4-(5-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octan-2-yl)-1,3,4-thiadiazol-2-yl)piperazine-1-carboxylate (180 mg, 0.36 mmol) and 10% Pd(OH)2 (1.8 g) in THF (10 mL) was stirred under H2 at rt for 8.5 hrs. The reaction mixture was then filtered and concentrated to give tert-butyl 4-(5-((2S,5R)-6-hydroxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octan-2-yl)-1,3,4-thiadiazol-2-yl)piperazine-1-carboxylate (133 mg, 90%) as a white solid. ESI-MS (EI+, m/z): 411.17 [M+H]+.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-5f0ff8d473b34150ab38d73fbcda6b67
Source dataset
uspto-grants-2015_03
Patent number
US08969570B2

Reaction notes

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