2-Propanethiol → HCID 68428603, compound

HRID 642568Notes

Reaction equation

HRID 642568 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([CH2:12]Br)[C:9]2[N:14]=[C:15]([C:17]([CH3:20])([CH3:19])[CH3:18])[S:16][C:8]=2[C:7]=1[O:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])=[O:5])[CH3:2].[CH3:28][CH:29]([SH:31])[CH3:30].C(=O)([O-])[O-].[Cs+].[Cs+].C1COCC1>C(OCC)(=O)C.C(O)C>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([CH2:12][S:31][CH:29]([CH3:30])[CH3:28])[C:9]2[N:14]=[C:15]([C:17]([CH3:20])([CH3:19])[CH3:18])[S:16][C:8]=2[C:7]=1[O:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 63642-PropanethiolHCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 68428368HCID 68428368, compound

Product 1

HCID 68428603HCID 68428603, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of the crude 4-bromomethyl-2-tert-butyl-7-(2,2-dimethyl-propionyloxy)-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (above), 2-propanethiol (75 μL, 0.8 mmol), and cesium carbonate (130 mg, 0.4 mmol) in 0.8 mL of a 1:1 mixture of THF:ethanol was stirred for 22 h. The resultant reaction mixture was diluted with ethyl acetate, and washed with water and brine. The organic fractions were dried over anhydrous sodium sulfate and concentrated under reduced pressure to 160 mg of the title compound. MS (ESI+): m/z 452.95 (M+1).

Workup

  1. customThe resultant reaction mixture
  2. washwashed with water and brine
  3. dry with materialThe organic fractions were dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure to 160 mg of the title compound

Sources & evidence

ORD record
ord-f21378e0c810461cb7d4c2429139fccf
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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