Hydrochloric Acid → HCID 9873179, compound

HRID 327407Notes

Reaction equation

HRID 327407 reaction equation
C([O:4][C:5](=[O:44])[C:6]([CH3:43])([CH3:42])[CH2:7][C:8]1[N:9]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)[C:10]2[C:15]([C:16]=1[S:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][C:13]([O:22][CH2:23][C:24]1[N:25]=[CH:26][C:27]3[C:32]([CH:33]=1)=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:12][CH:11]=2)C=C.CO.[Li+].[OH-].Cl>C1COCC1>[Cl:41][C:38]1[CH:37]=[CH:36][C:35]([CH2:34][N:9]2[C:10]3[C:15](=[CH:14][C:13]([O:22][CH2:23][C:24]4[N:25]=[CH:26][C:27]5[C:32]([CH:33]=4)=[CH:31][CH:30]=[CH:29][CH:28]=5)=[CH:12][CH:11]=3)[C:16]([S:17][C:18]([CH3:21])([CH3:19])[CH3:20])=[C:8]2[CH2:7][C:6]([CH3:43])([CH3:42])[C:5]([OH:44])=[O:4])=[CH:40][CH:39]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 53850656HCID 53850656, compound

Product 1

HCID 9873179HCID 9873179, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound from Step 1 (174 mg) was dissolved in THF (5 mL), MeOH (3 mL), 1N LiOH (1.3 mL) and heated at 65° C. for 1 hr. After cooling to r.t., the mixture was acidified with 1N HCl and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered, and evaporated to dryness. The residue was purified by silica gel chromatography eluting first with 1:1 EtOAc/hexane and followed by the addition of 5% HOAc to this solvent. The title compound (126 mg), was obtained as a white solid; mp 227.5°-228.5° C.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by silica gel chromatography
  7. washeluting first with 1:1 EtOAc/hexane
  8. additionfollowed by the addition of 5% HOAc to this solvent

Sources & evidence

ORD record
ord-90794dc2e4b94d4fbe3888d7f11cf9d7
Source dataset
uspto-grants-1993_12
Patent number
US05273980

Reaction notes

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