Hydrochloric Acid → HCID 53961705, compound

HRID 2269322Notes

Reaction equation

HRID 2269322 reaction equation
[C:1]([O:5][C:6](=[O:33])[CH:7]([NH:14][S:15]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[CH:20][CH:19]=1)(=[O:17])=[O:16])CCCC(=O)C)([CH3:4])([CH3:3])[CH3:2].[CH3:34][C:35](C)([O-:37])[CH3:36].[K+].Cl.[CH2:41]1COC[CH2:42]1>O>[C:1]([O:5][C:6]([CH:7]1[C:35]([OH:37])([CH3:36])[CH2:34][CH2:42][CH2:41][N:14]1[S:15]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)=[CH:20][CH:19]=1)(=[O:16])=[O:17])=[O:33])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 23665647Potassium tert-butoxideHCID 54209562HCID 54209562, compound

Product 1

HCID 53961705HCID 53961705, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-[4-(4-fluoro-benzyloxy)-benzenesulfonylamino]6-oxo-heptanoic acid tert-butyl ester (0.70 g, 1.5 mmol) in 6 mL of THF was added potassium tert-butoxide (0.7 mL of a 1M solution in THF, 0.70 mmol). After stirring for 24 h at room temperature, the mixture was diluted with water, acidified with 1M HCl and extracted 3× into ethyl acetate. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. Filtration of the residue through a pad of silica gel eluting with 1:1 ethyl acetate-hexane afforded 1-[4-(4-fluoro-benzyloxy)-benzenesulfonyl]-3-hydroxy-3-methyl-piperidine-2-carboxylic acid tert-butyl ester as a mixture of diastereomers. Separation of the diastereomers by radial chromatography (1-4% acetone-CH2Cl2, 4 mm plate) afforded 0.12 g of each diastereomer as a colorless oil.

Workup

  1. extractionextracted 3× into ethyl acetate
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. filtrationFiltration of the residue through a pad of silica gel eluting with 1:1 ethyl acetate-hexane

Sources & evidence

ORD record
ord-7dc981b6f5ae40dabf6198939e4fb520
Source dataset
uspto-grants-2001_12
Patent number
US06329397B1

Reaction notes

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