Potassium Carbonate → p-methoxybenzyl 5-acetoxy-methyl-6H-1,3-thiazine-4-carboxylate

HRID 1657999Notes

Reaction equation

HRID 1657999 reaction equation
[CH:1]([NH:3][CH:4](P(OCC)(OCC)=O)[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)=[O:6])=[S:2].[C:25](=O)([O-])[O-].[K+].[K+].[C:31]([O:34][CH2:35][C:36](=O)CCl)(=[O:33])[CH3:32]>CC(C)=O>[C:31]([O:34][C:35]1[CH2:36][S:2][C:1]([CH3:25])=[N:3][C:4]=1[C:5]([O:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1)=[O:6])(=[O:33])[CH3:32]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 384132-Propanone, 1-(acetyloxy)-3-chloro-HCID 12866380HCID 12866380, compound

Product 1

HCID 68133590p-methoxybenzyl 5-acetoxy-methyl-6H-1,3-thiazine-4-carboxylateYield 105.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a stirring solution of p-methoxybenzyl α-thioformamido-diethylphosphonoacetate (114 mg., 0.3 mmole) in acetone (1.5 ml) is added powdered potassium carbonate (124 mg, 0.9 mmole). The resulting mixture is stirred for 5 minutes at room temperature and under a nitrogen atmosphere, then treated with a solution of 1-acetoxy-3-chloro-2-propanone (48 mg, 0.32 mmole) in acetone (0.5 ml). After having been sitrred for 3 hours at room temperature, the mixture is filtered to remove the salts which are washed with acetone. The combined filtrate and washings are evaporated in vacuo to a dark oil. The residue is dissolved in CCl4 (6 ml), washed with aqueous phosphate (1 ml of 1M dipotassium phosphate + 2 ml water) and water (2 × 3 ml)., dried over magnesium sulfate, and evaporated in vacuo to give crude p-methoxybenzyl 5-acetoxy-methyl-6H-1,3-thiazine-4-carboxylate (106 mg) as an orange oil.

Workup

  1. waitAfter having been sitrred for 3 hours at room temperature
  2. filtrationthe mixture is filtered
  3. customto remove the salts which
  4. washare washed with acetone
  5. customThe combined filtrate and washings are evaporated in vacuo to a dark oil
  6. dissolutionThe residue is dissolved in CCl4 (6 ml)
  7. washwashed with aqueous phosphate (1 ml of 1M dipotassium phosphate + 2 ml water) and water (2 × 3 ml)
  8. dry with material, dried over magnesium sulfate
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-d65410483acd4fc7a8657101b1a30004
Source dataset
uspto-grants-1976_06
Patent number
US03962224

Reaction notes

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