Hydrochloric Acid → HCID 86601016, compound

HRID 1796797Notes

Reaction equation

HRID 1796797 reaction equation
[C:1]([O:5][C:6](=[O:32])[CH2:7][N:8](S(C1C=CC(OCC2C=CC=CC=2)=CC=1)(=O)=O)[CH2:9][CH2:10][CH2:11][C:12](=[O:14])[CH3:13])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].Cl>O1CCCC1.O>[C:1]([O:5][C:6]([CH:7]1[C:12]([OH:14])([CH3:13])[CH2:11][CH2:10][CH2:9][NH:8]1)=[O:32])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 69597616HCID 69597616, compound2×

Product 1

HCID 86601016HCID 86601016, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution [(4-benzyloxy-benzenesulfonyl)-(4-oxo-pentyl)-amino]-acetic acid tert-butyl ester (compound of formula XVII, 25 g, 56 mmol) in 200 ml of tetrahydrofuran was added potassium tert-butoxide (24 ml of a 1M solution in tetrahydrofuran, 24 mmol). After stirring for about 24 hours at a temperature of about 20° C. to about 25° C., the mixture was diluted with water, acidified with 1M hydrochloric acid and extracted 3 times into ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The stereoisomers were separated by preparative HPLC on a Chiralpak AD column® eluting with 2-propanol-hexane, affording approximately 4 g of each stereoisomer of 1-[4-benzyloxy)-benzenesulfonyl]-3-hydroxy-3-methyl-piperidine-2-carboxylic acid tert-butyl ester (compound of formula XVIII) as a colorless oil.

Workup

  1. extractionextracted 3 times into ethyl acetate
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe stereoisomers were separated by preparative HPLC on a Chiralpak AD column®
  6. washeluting with 2-propanol-hexane

Sources & evidence

ORD record
ord-072f0bff175e461f8488720f6b1e84a7
Source dataset
uspto-grants-2006_04
Patent number
US07030242B2

Reaction notes

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