Hydrochloric Acid → HCID 57974053, compound

HRID 1367141Notes

Reaction equation

HRID 1367141 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[CH2:14][S:13](=[O:15])[CH2:12][C:11](=[O:16])[N:10]2[CH2:17][C:18]([O:20]CC2C=CC=CC=2)=[O:19])[CH:5]=[C:6]([F:8])[CH:7]=1.Cl.[Na+].[Cl-]>CO.C(=O)(O)[O-].[Na+].CCOCC>[F:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[CH2:14][S:13](=[O:15])[CH2:12][C:11](=[O:16])[N:10]2[CH2:17][C:18]([OH:20])=[O:19])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 57974070HCID 57974070, compound

Product 1

HCID 57974053HCID 57974053, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of benzyl [(3R)-3-(3,5-difluorophenyl)-1-oxido-5-oxothiomorpholin-4-yl]acetate (93.6 mg, 0.238 mmol, major isomer, from Step B) in MeOH (5 mL) was purged with nitrogen. The septum sealing the reaction vessel was briefly removed to allow introduction of Pd/C (˜18 mg, 10% Pd/C). The vessel was then purged with hydrogen from a balloon, before a fresh balloon of hydrogen was attached. After LCMS analysis indicated that the reaction had stalled at 60% conversion, the hydrogen atmosphere was replaced with nitrogen. The mixture was then filtered through a pad of celite, washing with MeOH as needed. The filtrate was concentrated in vacuo to provide a residue which was diluted with aqueous sodium bicarbonate (2%) and ether. The aqueous layer was extracted with ether (4 times) to remove un-reacted starting material. The aqueous layer was then made acidic by the addition of 3M HCl, and was then saturated with NaCl. This acidic aqueous layer was then extracted three times with DCM and three times with EtOAc. Both organics were dried over sodium sulfate, filtered and concentrated in vacuo to give the title compound. MS: m/z=304 (M+1).

Workup

  1. customwas briefly removed
  2. customThe vessel was then purged with hydrogen from a balloon, before a fresh balloon of hydrogen
  3. filtrationThe mixture was then filtered through a pad of celite
  4. washwashing with MeOH
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto provide a residue which
  7. extractionThe aqueous layer was extracted with ether (4 times)
  8. customto remove
  9. customun-reacted
  10. extractionThis acidic aqueous layer was then extracted three times with DCM and three times with EtOAc
  11. dry with materialBoth organics were dried over sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ef790ce990df4d1a93e8abf78114afbf
Source dataset
uspto-grants-2011_02
Patent number
US07893079B2

Reaction notes

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