Sulfuric acid hydrate (1:1) → 2-Chloro-5-(morpholin-4-ylcarbonyl)-1,3-thiazole-4-carboxylic acid

HRID 1948358Notes

Reaction equation

HRID 1948358 reaction equation
[Si]([O:8][CH2:9][C:10]1[N:11]=[C:12]([Cl:23])[S:13][C:14]=1[C:15]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=[O:16])(C(C)(C)C)(C)C.O.[OH:25]S(O)(=O)=O>CC(C)=O.C(O)(C)C.O>[Cl:23][C:12]1[S:13][C:14]([C:15]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[O:16])=[C:10]([C:9]([OH:8])=[O:25])[N:11]=1

Participants

6

Reactant 2

HCID 21910475Sulfuric acid hydrate (1:1)HCID 685182184-{[4-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloro-1,3-thiazol-5-yl]carbonyl}morpholine2×

Product 1

HCID 685138662-Chloro-5-(morpholin-4-ylcarbonyl)-1,3-thiazole-4-carboxylic acid

Reagents, catalysts & solvents 3

HCID 3776IsopropanolCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of 173 mg (1.7 mmol) CrO3 in 1 ml of 4:1 water/H2SO4 was added to as solution of 310 mg (0.82 mmol) of 4-{[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloro-1,3-thiazol-5-yl]carbonyl}morpholine (Intermediate 216) in 3 ml acetone cooled in an ice water bath. The mixture was stirred with warming room temperature over 90 min. A few drops of isopropanol were added, and the mixture was diluted with water and extracted 2 times with EtOAc. The EtOAc extracts were washed with brine, dried (MgSO4) and concentrated to give 190 mg of a white solid. MS (ES) (MH+): 277 for C9H9ClN2O4S; NMR (d6-DMSO): 3.3 (m, 4H), 3.6 (m, 4H), 13.7 (s, 1H).

Workup

  1. temperaturecooled in an ice water bath
  2. extractionextracted 2 times with EtOAc
  3. washThe EtOAc extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-45baf6033393426bb9f0b01baf9cc96b
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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