HCID 57974070, compound → HCID 57974053, compound

HRID 1866619Notes

Reaction equation

HRID 1866619 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>CO>[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

3

Reactant 1

HCID 57974070HCID 57974070, compound

Product 1

HCID 57974053HCID 57974053, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of benzyl [(3R)-3-(3,5-difluorophenyl)-1-oxido-5-oxothiomorpholin-4-yl]acetate (24.5 mg, 0.062 mmol, minor isomer, from the preparation of Intermediate 4, Step B) in MeOH (2 mL) was purged with nitrogen. The septum sealing the reaction vessel was briefly removed to allow introduction of Pd/C (˜6 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 was progressing slowly, a suspension of 10% Pd/C was introduced via syringe. After 2.25 hours 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 the title compound, which was used without further purification. MS: m/z=304 (M+1).

Workup

  1. customwas purged with nitrogen
  2. customwas briefly removed
  3. customThe vessel was then purged with hydrogen from a balloon, before a fresh balloon of hydrogen
  4. additiona suspension of 10% Pd/C
  5. additionwas introduced via syringe
  6. filtrationThe mixture was then filtered through a pad of celite
  7. washwashing with MeOH
  8. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-66a47ed0e4874a279b785063ed8ca964
Source dataset
uspto-grants-2009_12
Patent number
US07629338B2

Reaction notes

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