Hydrochloric Acid → HCID 89525460, compound

HRID 1523299Notes

Reaction equation

HRID 1523299 reaction equation
C(S([NH:7][C:8]1([CH:12]([CH3:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][O:10][CH2:9]1)=O)(C)(C)C.Cl.[OH-].[Na+].Cl[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>CO.O1CCOCC1>[CH2:26]([O:25][C:23]([NH:7][C:8]1([CH:12]([CH3:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9][O:10][CH2:11]1)=[O:24])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 89525434HCID 89525434, compound

Product 1

HCID 89525460HCID 89525460, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 2-{3-[(tert-butylsulfinyl)amino]oxetan-3-yl}propanoate (Preparation 34, 40 g, 140 mmol) in methanol (400 mL) at 0° C. was added a 4M solution of hydrogen chloride in 1,4-dioxane (72 mL). After 2 hours, a 4M aqueous solution of sodium hydroxide (400 mL) was added drop-wise until pH 7 was achieved whilst maintaining the temperature at 0° C. The methanol was removed in vacuo. The resulting solution was stirred with tetrahydrofuran (150 mL) and a 1M aqueous solution of sodium hydrogen carbonate (180 mL) at 0° C. Benzyl chloroformate (33.7 g, 187 mmol) was added and the reaction mixture stirred at room temperature for 18 hours. The organics were removed in vacuo and the resulting solution extracted with dichloromethane. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography to afford the title compound.

Workup

  1. customThe methanol was removed in vacuo
  2. customat 0° C
  3. stirringthe reaction mixture stirred at room temperature for 18 hours
  4. customThe organics were removed in vacuo
  5. extractionthe resulting solution extracted with dichloromethane
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d1791852419c445485b04c96ca9d599a
Source dataset
uspto-grants-2015_07
Patent number
US09079878B2

Reaction notes

Loading…