Hydrochloric Acid → HCID 54212248, compound

HRID 234220Notes

Reaction equation

HRID 234220 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[NH:18][C:17](=[O:19])[CH2:16][CH2:15][C@@H:14]([O:20]C(OCC)=O)[CH2:13][O:12][C:11](=[O:26])[C:10]2[C:27]([CH3:41])=[C:28]([O:39][CH3:40])[CH:29]=[C:30]([O:31][Si](C(C)(C)C)(C)C)[C:9]=2[CH2:8][S:7][CH2:6]1)=[O:4].Cl>C[O-].[Na+].CO>[CH3:1][O:2][C:3]([C@H:5]1[NH:18][C:17](=[O:19])[CH2:16][CH2:15][C@@H:14]([OH:20])[CH2:13][O:12][C:11](=[O:26])[C:10]2[C:27]([CH3:41])=[C:28]([O:39][CH3:40])[CH:29]=[C:30]([OH:31])[C:9]=2[CH2:8][S:7][CH2:6]1)=[O:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 54452724HCID 54452724, compound

Product 1

HCID 54212248HCID 54212248, compoundYield 35.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

Procedure

A solution of 20 mg of (4R,9R)-16-(tert-butyl-dimethylsilanyloxy)-9-ethoxycarbonyloxy-14-methoxy-13-methyl-6, 12-dioxo-1,3,4,5,6,7,8,9,10,12-decahydro-11,2,5-benzoxathiaazacyclotetradecine-4-carboxylic acid methyl ester was subjected in an analogous manner to the procedure described in Example 1. The crude product was dissolved in 0.5 ml of a 0.6M solution of sodium methoxide in methanol. The solution was stirred at 0° C. for 7 min whereupon 2 ml of 1N hydrochloric acid were added. The mixture was extracted with ethyl acetate and the organic layer was washed with water, dried over sodium sulfate and evaporated in vacuo. The residue was crystallized from ethyl acetate/hexane to afford 5 mg of (4R,9R)-9,16-dihydroxy-14-methoxy-13-methyl-6,12-dioxo-1,3,4,5,6,7,8,9,10,12-decahydro-11,2,5-benzoxathiaazacyclotetradecine-4-carboxylic acid methyl ester as a white solid.

Workup

  1. additionwere added
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-57ba10d70e2640cc90dc9702fb39bdf6
Source dataset
uspto-grants-1997_01
Patent number
US05594135

Reaction notes

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