Water → HCID 11260214, compound

HRID 2104259Notes

Reaction equation

HRID 2104259 reaction equation
[CH2:1]([N:3]([CH:18]1[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([S:27][C:28]([CH3:37])([CH3:36])[C:29]([O:31]C(C)(C)C)=[O:30])[CH:24]=2)[CH2:19]1)[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]([F:17])([F:16])[F:15])=[CH:9][CH:8]=1)=[O:5])[CH3:2].S(=O)(=O)(O)O.O>C(OC(C)C)(=O)C>[CH2:1]([N:3]([C@H:18]1[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([S:27][C:28]([CH3:36])([CH3:37])[C:29]([OH:31])=[O:30])[CH:24]=2)[CH2:19]1)[C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][C:14]([F:17])([F:15])[F:16])=[CH:11][CH:12]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 68812777HCID 68812777, compound

Product 1

HCID 11260214HCID 11260214, compound

Reagents, catalysts & solvents 1

HCID 7915Isopropyl AcetateSolvent

Conditions

Temperature
17.5 °C

Procedure

To a solution of tert-butyl 2-{2-[1-ethyl-3-(4-trifluoromethoxy-phenyl)-ureido]-indan-5-ylsulfanyl}-2-methyl-propionate (288 g, 0.534 mol) was added a solution of sulfuric acid (535 g, 5.34 mol) in isopropyl acetate (0.7 L) while maintaining the reaction temperature at about 15-20° C. The clear solution was stirred at 15° C. for 1 hour after the addition. To the reaction mixture was added cold water (0.94 L). After removal of the acidic aqueous layer, the isopropyl acetate layer was washed until the pH of the aqueous layer reached 3. The solution was used in the next step without isolation.

Workup

  1. additionafter the addition
  2. customAfter removal of the acidic aqueous layer
  3. washthe isopropyl acetate layer was washed until the pH of the aqueous layer

Sources & evidence

ORD record
ord-d58794b12120419dafefd5f468c81626
Source dataset
uspto-grants-2009_08
Patent number
US07576238B2

Reaction notes

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