Acetic Acid → HCID 69748888, compound

HRID 1062406Notes

Reaction equation

HRID 1062406 reaction equation
C(O)(=O)C.[O-:5][C:6]#[N:7].[Na+].[Cl:9][C:10]1[CH:15]=[C:14]([S:16][C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=2)[CH:13]=[CH:12][C:11]=1[NH:24][C:25](=[O:36])[C@:26]([O:32][C:33](=[O:35])[CH3:34])([CH3:31])[C:27]([F:30])([F:29])[F:28]>C1COCC1.O>[Cl:9][C:10]1[CH:15]=[C:14]([S:16][C:17]2[CH:18]=[CH:19][C:20]([NH:23][C:6]([NH2:7])=[O:5])=[CH:21][CH:22]=2)[CH:13]=[CH:12][C:11]=1[NH:24][C:25](=[O:36])[C@:26]([O:32][C:33](=[O:35])[CH3:34])([CH3:31])[C:27]([F:30])([F:28])[F:29]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 517096Sodium CyanateHCID 57100558HCID 57100558, compound

Product 1

HCID 69748888HCID 69748888, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Water (0.34 ml), acetic acid (0.54 ml) and sodium cyanate (0.104 g dissolved in 0.3 ml of water) were added to a solution of (R)-N-[2-chloro-4-{4-aminophenylsulphanyl}phenyl]-2-acetoxy-2-methyl-3,3,3-trifluoropropanamide (0.432 g) (Method 22) in THF (0.8 ml. The mixture was stirred for 2 hours then diluted with water (5 ml) and extracted with ethyl acetate (2×20 ml). The extracts were poured onto a Varian Chem Elut column and eluted with ethyl acetate. Volatile material was removed by evaporation and the residue was triturated with ether to give the title compound (0.31 g) as a solid. NMR: 1.8 (s, 3H), 2.2 (s, 3H), 5.9 (s, 2H), 7.1 (s, 3H), 7.4 (d, 2H), 7.5 (d, 2H). 8.8 (s, 1H), 9.9 (s, 1H); MS (ESP−): 474.

Workup

  1. extractionextracted with ethyl acetate (2×20 ml)
  2. additionThe extracts were poured onto a Varian Chem Elut column
  3. washeluted with ethyl acetate
  4. customVolatile material was removed by evaporation
  5. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-e4d489539a93466f816b2ac03043de90
Source dataset
uspto-grants-2005_11
Patent number
US06960688B2

Reaction notes

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