Ethyl Acetate → HCID 68408299, compound

HRID 888037Notes

Reaction equation

HRID 888037 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:34])[C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:24]3[S:33][CH:32]=[CH:31][C:25]=3[N:26]=[C:27](SC)[N:28]=2)=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:36]1C=CC=C(C(OO)=O)C=1.[S:46](S([O-])=O)([O-:49])(=O)=[O:47].[Na+].[Na+].C(OCC)(=O)C>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:34])[C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:24]3[S:33][CH:32]=[CH:31][C:25]=3[N:26]=[C:27]([S:46]([CH3:36])(=[O:49])=[O:47])[N:28]=2)=[CH:19][CH:18]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acid2×HCID 656671Sodium PyrosulfiteHCID 68408160HCID 68408160, compound

Product 1

HCID 68408299HCID 68408299, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cooled (0° C.) solution of N-(2-t-butoxycarbonylaminophenyl)-4-[2-(methylthio)thieno[3,2-d]pyrimidin-4-yl]benzamide (Method 55, 960 mg, 1.95 mg) in DMF (40 ml), was added meta-chloroperbenzoic acid (57%, 630 mg, 2.08 mmol) and the reaction mixture stirred, allowing warming to ambient temperature. After 3 hours a further portion of meta-chloroperbenzoic acid (70%, 589 mg, 2.40 mmol) was added and stirring continued for 2 hours. The reaction mixture was then carefully poured into aqueous sodium metabisulfite solution (0.25M, 100 ml), before addition of ethyl acetate (100 ml). The insoluble material was removed by filtration and dried in vacuo to yield the title compound (586 mg, 57%); NMR Spectrum: (DMSO-d6) 1.46 (s, 9H), 3.57 (s, 3H), 7.18 (t, 1H), 7.24 (t, 1H), 7.59 (m, 2H), 8.00 (d, 1H), 8.27 (d, 2H), 8.41 (d, 2H), 8.75 (s, 1H), 8.90 (d, 1H), 10.07 (s, 1H); Mass Spectrum: M+Na+ 547.

Workup

  1. stirringstirring
  2. customThe insoluble material was removed by filtration
  3. customdried in vacuo

Sources & evidence

ORD record
ord-45d3f414df0748669f75f5b73398b8ad
Source dataset
uspto-grants-2012_08
Patent number
US08247562B2

Reaction notes

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