Hydrochloric Acid → HCID 9892605, compound

HRID 1612898Notes

Reaction equation

HRID 1612898 reaction equation
C[CH:2]([C:9]1[N:10]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)[C:11]2[C:16]([C:17]=1[CH3:18])=[CH:15][C:14]([O:19][CH2:20][C:21]1[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=1)=[CH:13][CH:12]=2)[C:3]([CH3:8])([CH3:7])[C:4]([OH:6])=[O:5].C1COCC1.[Li+].[OH-].Cl>CO>[Cl:38][C:35]1[CH:36]=[CH:37][C:32]([CH2:31][N:10]2[C:11]3[C:16](=[CH:15][C:14]([O:19][CH2:20][C:21]4[CH:30]=[CH:29][C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[CH:22]=4)=[CH:13][CH:12]=3)[C:17]([CH3:18])=[C:9]2[CH2:2][C:3]([CH3:7])([CH3:8])[C:4]([OH:6])=[O:5])=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 19776888HCID 19776888, compound

Product 1

HCID 9892605HCID 9892605, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the ester from Step 1 (278 mg), 3 mL THF, 3 mL MeOH, and 2.7 mL 1N LiOH was stirred at 80° C. for 4 hours under nitrogen. The solution was cooled, poured onto 1N HCl, extracted 2× EtOAc, washed 2× brine, dried (MgSO4), and evaporated. Purification of the residue by chromatography (silica gel; hexane/EtOAc 2:1) gave the title compound as a solid, m.p. 151.5°-152.5° C.

Workup

  1. temperatureThe solution was cooled
  2. extractionextracted 2× EtOAc
  3. washwashed 2× brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customPurification of the residue by chromatography (silica gel; hexane/EtOAc 2:1)

Sources & evidence

ORD record
ord-2aa52b69366442bf9f30e1f85ee68e79
Source dataset
uspto-grants-1993_03
Patent number
US05190968

Reaction notes

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