Citric Acid → HCID 86645883, compound

HRID 2096858Notes

Reaction equation

HRID 2096858 reaction equation
FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.[Cl:16][C:17]1[CH:22]=[C:21](O)[CH:20]=[CH:19][C:18]=1[CH:24]([CH3:43])[C:25]([C:31]1[CH:42]=[CH:41][C:34]2[N:35]([CH3:40])[C:36](=[O:39])[CH2:37][O:38][C:33]=2[CH:32]=1)([OH:30])[C:26]([F:29])([F:28])[F:27].C(N(CC)CC)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl>[Cl:16][C:17]1[CH:22]=[C:21]([O:6][S:7]([C:10]([F:11])([F:12])[F:13])(=[O:8])=[O:9])[CH:20]=[CH:19][C:18]=1[CH:24]([CH3:43])[C:25]([OH:30])([C:31]1[CH:42]=[CH:41][C:34]2[N:35]([CH3:40])[C:36](=[O:39])[CH2:37][O:38][C:33]=2[CH:32]=1)[C:26]([F:28])([F:29])[F:27]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 66697111HCID 66697111, compound

Product 1

HCID 86645883HCID 86645883, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonic anhydride (0.12 ml) was added to 7-[2-(2-chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-4-methyl-4H-benzo[1,4]oxazin-3-one (150 mg, Example 158 step 2) and triethylamine (0.2 ml) in DCM (5 ml). The mixture was stirred for 2 h at room temperature. 10% aqueous citric acid was added and extracted with DCM. The combined organic layers were dried over Na2SO4 and then concentrated to give the title compound (140 mg) as light yellow foam. MS (m/e, ISP neg. ion)=546.2 [M−H+].

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9da6f2fa99704eee9285ecb0b8b368f1
Source dataset
uspto-grants-2013_05
Patent number
US08450313B2

Reaction notes

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