HCID 57974062, compound → HCID 57974065, compound

HRID 1866620Notes

Reaction equation

HRID 1866620 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[CH2:14][S:13](=[O:16])(=[O:15])[CH2:12][C:11](=[O:17])[N:10]2[CH2:18][C:19]([O:21]CC2C=CC=CC=2)=[O:20])[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])(=[O:16])[CH2:12][C:11](=[O:17])[N:10]2[CH2:18][C:19]([OH:21])=[O:20])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

3

Reactant 1

HCID 57974062HCID 57974062, compound

Product 1

HCID 57974065HCID 57974065, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of benzyl [(3R)-3-(3,5-difluorophenyl)-1,1-dioxido-5-oxothiomorpholin-4-yl]acetate (71.7 mg, 0.145 mmol, 83%, from Step A) in MeOH (3 mL) was purged with nitrogen. The septum sealing the reaction vessel was briefly removed to allow introduction of Pd/C (˜14 mg, 10% Pd/C). The vessel was then purged with hydrogen from a balloon, before a fresh balloon of hydrogen was attached. After 30 minutes 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. MS: m/z=320 (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

Sources & evidence

ORD record
ord-f1e5f64f9f0f412097a48dd4f7af4ebc
Source dataset
uspto-grants-2009_12
Patent number
US07629338B2

Reaction notes

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