Sulfuric Acid → HCID 178462009, compound

HRID 339921Notes

Reaction equation

HRID 339921 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]2[C:15]([CH3:17])([CH3:16])[O:14][C:13]([NH:18][C@H:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[CH3:20])=[N:12][S:11]2(=[O:29])=[O:28])[CH:5]=1.S(=O)(=O)(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O>[F:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C@@H:19]([NH:18][C:13]1[O:14][C:15]([CH3:16])([CH3:17])[CH:10]([C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([OH:30])=[O:2])[S:11](=[O:28])(=[O:29])[N:12]=1)[CH3:20]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 178497675HCID 178497675, compound

Product 1

HCID 178462009HCID 178462009, compoundYield 33,493%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-{2-[(S)-1-(2-fluorophenyl)ethylamino]-6,6-dimethyl-4,4-dioxo-5,6-dihydro-4H-4lambda*6*-[1,4,3]oxathiazin-5-yl}benzoic acid methyl ester (1.7 mg) in dioxane (15 ml) were added water (5 ml) and sulfuric acid (0.3 ml), and the mixture was stirred at 100° C. for 16 h. The mixture was alkalized with sodium carbonate solution, diluted with water and washed with ethyl acetate. The aqueous phase was acidified, extracted with ethyl acetate, dried over magnesium sulfate and concentrated. This gave the product (551 mg) with a molecular weight of 420.5 g/mol (C20H21FN2O5S).

Workup

  1. washwashed with ethyl acetate
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6b67edb144294989b7b074c3bf5c1286
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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