Trifluoroacetic acid → HCID 18442588, compound

HRID 458800Notes

Reaction equation

HRID 458800 reaction equation
C(OC([N:8]1[CH:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=2)[C:13]2[CH:26]=[C:27]([O:32][CH3:33])[C:28]([O:30][CH3:31])=[CH:29][C:12]=2[S:11](=[O:35])(=[O:34])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.O.[OH-].[Na+].C(Cl)Cl.CO>C(Cl)Cl>[CH3:25][O:24][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][C:19]=1[O:22][CH3:23])[CH2:15][CH:14]1[C:13]2[CH:26]=[C:27]([O:32][CH3:33])[C:28]([O:30][CH3:31])=[CH:29][C:12]=2[S:11](=[O:35])(=[O:34])[CH2:10][CH2:9][NH:8]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 21226129Dichloromethane methanolHCID 23719242Sodium hydroxide--water (1/1/1)HCID 69353488HCID 69353488, compound

Product 1

HCID 18442588HCID 18442588, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 9-(3,4-dimethoxy-benzyl)-2,3-dimethoxy-5,5-dioxo-5,6,7,9 tetrahydro-5λ6-thia-8-aza-benzocycloheptene-8-carboxylic acid tert-butyl ester (310 mg, 0.61 mmol) in dry CH2Cl2 (3 ml), was added trifluoroacetic acid (372 μL, 4.86 mmol). The resulting mixture was stirred at RT for 20 h under nitrogen. The reaction mixture was combined with water/NaOH 2N, extracted twice with CH2Cl2, and the combined organic phases were dried over anhydrous MgSO4, filtered and concentrated to give a crude oil. Flash chromatography (CH2Cl2/MeOH: 9/1) gave the title compound as a pale yellow oil (118 mg, 47%).

Workup

  1. extractionextracted twice with CH2Cl2
  2. dry with materialthe combined organic phases were dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude oil

Sources & evidence

ORD record
ord-db114610e907493e8e4ba196fd867258
Source dataset
uspto-grants-2007_03
Patent number
US07192950B2

Reaction notes

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