Ammonium fluoride → HCID 67713067, compound

HRID 234209Notes

Reaction equation

HRID 234209 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:15][O:14][CH2:13][C:12]2[C:16]([O:29][Si](C(C)(C)C)(C)C)=[CH:17][C:18]([O:21][Si](C(C)(C)C)(C)C)=[C:19]([CH3:20])[C:11]=2[C:10](=[O:37])[S:9][C@H:8]([CH3:38])[C:7](=[O:39])[NH:6]1)=[O:4].[F-].[NH4+]>CO>[CH3:1][O:2][C:3]([C@H:5]1[CH2:15][O:14][CH2:13][C:12]2[C:16]([OH:29])=[CH:17][C:18]([OH:21])=[C:19]([CH3:20])[C:11]=2[C:10](=[O:37])[S:9][C@H:8]([CH3:38])[C:7](=[O:39])[NH:6]1)=[O:4]

Participants

4

Reactant 2

HCID 25516Ammonium fluorideHCID 67713094HCID 67713094, compound

Product 1

HCID 67713067HCID 67713067, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 35 mg of (4R,7R)-11,13-bis-(tert-butyl-dimethylsilanyloxy)-7,10-dimethyl-6,9-dioxo-3,4,5,6,7,9-hexahydro-1H-8,2,5-benzoxathiaazacyclo-undecine-4-carboxylic acid methyl ester and 20 mg ammonium fluoride in 2 ml of methanol was stirred at room temperature for 1 h. The solvent was evaporated in vacuo and the residue was chromatographed on silica gel using ethyl acetate as eluent. The pure product was crystallized from dichloromethane to give 13 mg of (4R,7R)-11,13-dihydroxy-7,10-dimethyl-6,9-dioxo-3,4,5,6,7,9-hexahydro-1H-8,2,5-benzoxathiaazacycloundecine-4-carboxylic acid methyl ester as white crystals, m.p. 216°-218° C. (dec.).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was chromatographed on silica gel
  3. customThe pure product was crystallized from dichloromethane

Sources & evidence

ORD record
ord-d74016e1ba614a4eae775424d3d6981b
Source dataset
uspto-grants-1997_01
Patent number
US05594135

Reaction notes

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