Thioglycolic Acid → HCID 86700673, compound

HRID 1406858Notes

Reaction equation

HRID 1406858 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([N:14]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)[CH2:11][CH2:10][C@H:9]1[C:35]1[N:39]=[CH:38][O:37][N:36]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].SCC(O)=O.O[Li].O.CCOC(C)=O>CN(C=O)C>[CH2:28]([O:27][NH:14][C@H:12]1[CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C@H:9]([C:35]2[N:39]=[CH:38][O:37][N:36]=2)[CH2:10][CH2:11]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 1133Thioglycolic AcidHCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 86700671HCID 86700671, compound

Product 1

HCID 86700673HCID 86700673, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of (2S,5R)-tert-butyl5-(N-(benzyloxy)-2-nitrophenylsulfonamido)-2-(1,2,4-oxadiazol-3-yl)piperidine-1-carboxylate (1.5 g, 2.683 mmol), HSCH2COOH (1.48 g, 16.1 mmol), LiOH.H2O (1.13 g, 26.83 mmol) in DMF (50 mL) was stirred at 30° C. for 17 hrs. EtOAc (150 mL) was then added and the mixture was washed with water (2×), and saturated sodium chloride (2×), dried over Na2SO4, and concentrated. The residue was purified by silica gel column chromatography (gradient elution 0˜50% petroleum ether/EtOAc) to give (2S,5R)-tert-butyl 5-(benzyloxyamino)-2-(1,2,4-oxadiazol-3-yl)piperidine-1-carboxylate (700 mg, 63%) as a pale yellow solid. ESI-MS (EI+, m/z): 375.0 [M+H]+.

Workup

  1. washthe mixture was washed with water (2×), and saturated sodium chloride (2×)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (gradient elution 0˜50% petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-56f0ae276ade4660b4a750af9b6df431
Source dataset
uspto-grants-2014_12
Patent number
US08916709B2

Reaction notes

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