Tetrabutylammonium Fluoride → HCID 86590885, compound

HRID 891802Notes

Reaction equation

HRID 891802 reaction equation
[CH3:1][O:2][C:3](=[O:40])[C@@H:4]([NH:24][C:25]([N:27]1[CH2:30][CH:29]([O:31][C:32](=[O:39])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:28]1)=[S:26])[CH2:5][O:6][Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][O:2][C:3](=[O:40])[C@@H:4]([NH:24][C:25]([N:27]1[CH2:28][CH:29]([O:31][C:32](=[O:39])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:30]1)=[S:26])[CH2:5][OH:6]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86590884HCID 86590884, compound

Product 1

HCID 86590885HCID 86590885, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (2S)-2-{[3-(benzoyloxy)-azetidine-1-carbothioyl]amino}-3-(t-butyldiphenylsilyloxy)propionic acid methyl ester (23.3 g, 40.0 mmol) (obtained as described in Reference Example 70(3)) in tetrahydrofuran (700 ml) was added a 1.0 M solution of tetra-n-butylammonium fluoride in tetrahydrofuran (48.4 g, 48.4 mmol) in an ice bath and the mixture was stirred overnight. After checking the completion of the reaction, the mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using toluene:acetonitrile (3:1) as the eluant to afford (2S)-2-{[3-(benzoyloxy)-azetidine-1-carbothioyl]amino}-3-hydroxy-propionic acid methyl ester (12.6 g, yield 92%) as a white solid.

Workup

  1. customthe completion of the reaction
  2. customthe mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride solution
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-f3de140252d848d8aa734d14be45de89
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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