Tetrabutylammonium Fluoride → HCID 89832310, compound

HRID 338127Notes

Reaction equation

HRID 338127 reaction equation
[C:1]([NH:9][C:10]1[S:11][CH2:12][CH:13]2[CH2:18][N:17]([C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[CH2:16][C:14]2([C:29]2[S:33][C:32]([Si](C)(C)C)=[N:31][CH:30]=2)[N:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.O>[C:1]([NH:9][C:10]1[S:11][CH2:12][CH:13]2[CH2:18][N:17]([C:19]([O:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[O:20])[CH2:16][C:14]2([C:29]2[S:33][CH:32]=[N:31][CH:30]=2)[N:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 89823452HCID 89823452, compound

Product 1

HCID 89832310HCID 89832310, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of racemic benzyl 2-benzamido-7a-(2-trimethylsilylthiazol-5-yl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate (117 mg, 212 μmoles) in tetrahydrofuran (4 mL) is added 1 N tetrabutylammonium fluoride (1 N in tetrahydrofuran) (425 μL, 425 μmoles) and the mixture is stirred under nitrogen for one hour. The solution is diluted with water, extracted with ethyl acetate (3×), dried over sodium sulfate and concentrated. The crude product is purified over silica gel eluting with ethyl acetate/hexanes (5% to 100%) to give the title compound (89 mg, 88%). ES/MS (m/e): 479 (M+H).

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe crude product is purified over silica gel eluting with ethyl acetate/hexanes (5% to 100%)

Sources & evidence

ORD record
ord-157bfe7b9b244ea09d94e9a3848e00f0
Source dataset
uspto-grants-2014_11
Patent number
US08889856B2

Reaction notes

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