Hydrochloric Acid → HCID 131720905, compound

HRID 400099Notes

Reaction equation

HRID 400099 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][S:14][CH:15]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[CH2:19][CH2:18][C:17]3[CH:26]=[CH:27][CH:28]=[CH:29][C:16]2=3)[CH2:7]1)=[O:5])C.[OH-].[Na+].[ClH:32]>C(O)C>[ClH:32].[CH:26]1[C:17]2[CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[CH:15]([S:14][CH2:13][CH2:12][N:8]3[CH2:9][CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7]3)[C:16]=2[CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86753266HCID 86753266, compound

Product 1

HCID 131720905HCID 131720905, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above ester (1.23 g, 0.003 mol) was dissolved in ethanol (15 ml). 2 N Sodium hydroxide (4.0 ml) was added and the mixture was stirred for 1 h at room temperature. The solution was made acidic (pH 1) by addition of excess 1 N hydrochloric acid and concentrated in vacuo to remove ethanol. The remainder was extracted with diethyl ether (50 ml) and redissolved in dichloromethane (50 ml). The organic phase was dried (Na2SO4) and concentrated in vacuo. Crystallisation of the remainder from acetone (20 ml) afforded 0.78 g (62%) of the title compound as a crystalline powder.

Workup

  1. concentrationconcentrated in vacuo
  2. customto remove ethanol
  3. extractionThe remainder was extracted with diethyl ether (50 ml)
  4. dissolutionredissolved in dichloromethane (50 ml)
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customCrystallisation of the remainder from acetone (20 ml)

Sources & evidence

ORD record
ord-a952ddfa57cb4a28b396244e26244943
Source dataset
uspto-grants-1998_10
Patent number
US05827856

Reaction notes

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