Hydrochloric Acid → HCID 86701390, compound

HRID 870846Notes

Reaction equation

HRID 870846 reaction equation
[CH2:1]([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]([NH:20][NH:21]C(OC(C)(C)C)=O)=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:29].CCOCC>O1CCOCC1>[ClH:29].[CH2:1]([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]([NH:20][NH2:21])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86701380HCID 86701380, compound

Product 1

HCID 86701390HCID 86701390, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of tert-butyl 2-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)hydrazinecarboxylate (0.78 g, 2.0 mmol) in dioxane (10 mL) was added 4M HCl in dioxane (5 mL) at 0° C. The reaction mixture was stirred at rt for 1 h, then, Et2O (10 mL) was added. The solid precipitation was collected by filtration, washed with Et2O (2×), and dried under vacuum to provide (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbohydrazide hydrochloride (0.65 g, 99%), which was used directly in the next step. ESI-MS (EI+, m/z): 291.19 [M+H]+.

Workup

  1. customThe solid precipitation
  2. filtrationwas collected by filtration
  3. washwashed with Et2O (2×)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-4bfcf5f0e257489cab7538d943cfd1a3
Source dataset
uspto-grants-2015_03
Patent number
US08969570B2

Reaction notes

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