HCID 22103555, compound → HCID 22103503, compound

HRID 1457212Notes

Reaction equation

HRID 1457212 reaction equation
[C:1]1([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:6]=[CH:5][C:4]([O:7][CH2:8][C:9]2[CH:14]=[C:13]([C:15]3[O:16][CH:17]=[CH:18][N:19]=3)[CH:12]=[CH:11][C:10]=2[C:20]2[C:21]([S:26]([N:29]([C:36]3[O:40][N:39]=[C:38]([CH3:41])[C:37]=3[CH3:42])COCCOC)(=[O:28])=[O:27])=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:3][CH:2]=1>CCO.Cl>[C:1]1([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:2]=[CH:3][C:4]([O:7][CH2:8][C:9]2[CH:14]=[C:13]([C:15]3[O:16][CH:17]=[CH:18][N:19]=3)[CH:12]=[CH:11][C:10]=2[C:20]2[C:21]([S:26]([NH:29][C:36]3[O:40][N:39]=[C:38]([CH3:41])[C:37]=3[CH3:42])(=[O:28])=[O:27])=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 22103555HCID 22103555, compound

Product 1

HCID 22103503HCID 22103503, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of the title compound of Step (A) in 3 ml of 95% EtOH, 3 ml 6N HCl was added. The reaction was refluxed for 1 h and 10 min and concentrated. The residue was neutralized to pH>8 with NaHCO3, and was then acidified to pH 5 with aq. NaHSO4, and extracted with 3×20 ml EtOAc. The organic extracts were washed with brine, dried and concentrated. The residue was chromatographed on silica gel using 70:30:0.25 hexane/EtOAc/AcOH to furnish the title compound of this Example (45 mg, 75% for two steps) as a light yellow solid, m.p. 95°-105° C. (amorphous).

Workup

  1. temperatureThe reaction was refluxed for 1 h and 10 min
  2. concentrationconcentrated
  3. extractionextracted with 3×20 ml EtOAc
  4. washThe organic extracts were washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel using 70:30:0.25 hexane/EtOAc/AcOH

Sources & evidence

ORD record
ord-3070475ccdf4436a840f57e88b1c3ad1
Source dataset
uspto-grants-1998_12
Patent number
US05846990

Reaction notes

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