Hydrochloric Acid → HCID 86750898, compound

HRID 1682557Notes

Reaction equation

HRID 1682557 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[CH:16]3[CH2:17][O:18][C:19]([CH3:23])([CH3:22])[O:20][CH2:21][CH:15]23)(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[OH-:24].[K+].Cl>O>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C@@H:15]2[CH2:21][O:20][C:19]([CH3:23])([CH3:22])[O:18][CH2:17][C@H:16]2[OH:24])(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 15197407HCID 15197407, compound

Product 1

HCID 86750898HCID 86750898, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-(4-acetylaminobenzenesulfonyl)-4,4-dimethyl-1a,2,6,6a-tetrahydro-1H,4H-[1,3]-dioxepino[5,6-b]azirine (0.33 g), potassium hydroxide (0.14 g) and water (2.6 ml) was boiled with reflux for 60 minutes. The mixture was cooled to room temperature, acidified with diluted hydrochloric acid to pH 6.5 and evaporated to dryness at reduced pressure. The chromatography of the evaporation residue on a silica gel column by elution with a mixture of ethyl acetate/methanol (9.8:0.2) yielded trans-6-(4-acetylaminobenzene-sulfonamido)-2.2-dimethyl-1,3-dioxepane-5-ol, m.p. 203°-205° C./methylene chloride- methanol (9:1), and trans-6-sulfanylamido-2,2-dimethyl-1,3-dioxepane-5-ol.

Workup

  1. temperaturewith reflux for 60 minutes
  2. customevaporated to dryness at reduced pressure
  3. washThe chromatography of the evaporation residue on a silica gel column by elution
  4. additionwith a mixture of ethyl acetate/methanol (9.8:0.2)

Sources & evidence

ORD record
ord-7c6c60915891461db0f65b39c251853b
Source dataset
uspto-grants-1997_06
Patent number
US05635529

Reaction notes

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