Hydrochloric Acid → HCID 13091035, compound

HRID 435398Notes

Reaction equation

HRID 435398 reaction equation
[NH:1]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C@H:2]([C:12]([NH:14][C@H:15]([C:20]([N:22]1[CH2:36][CH2:35][CH2:34][C@H:23]1[C:24]([O:26]CC1C=CC=CC=1)=[O:25])=[O:21])[CH2:16][CH:17]([CH3:19])[CH3:18])=[O:13])[CH2:3][O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-].[Na+].Cl>C(O)C>[NH:1]([C:37]([O:39][C:40]([CH3:42])([CH3:41])[CH3:43])=[O:38])[C@H:2]([C:12]([NH:14][C@H:15]([C:20]([N:22]1[CH2:36][CH2:35][CH2:34][C@H:23]1[C:24]([OH:26])=[O:25])=[O:21])[CH2:16][CH:17]([CH3:19])[CH3:18])=[O:13])[CH2:3][O:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13091033HCID 13091033, compound

Product 1

HCID 13091035HCID 13091035, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The substance [18] (81 g, 135.5 mM) was dissolved in ethanol (300 ml). 1 N NaOH (176.15 ml, 1.3 molar excess) was added dropwise at 0° C. during 30 minutes and the mixture was stirred at room temperature for three hours. The reaction mixture was neutralized by adding 1 N HCl at 0° C. and ethanol was distilled off in vacuo. Water (300 ml) was added to the aqueous layer, which was then washed twice with ether, and 1 N HCl (150 ml) was at 0° C. and the mixture was extracted with ethyl acetate (400 ml). The ethyl acetate layer was washed with water, dried with anhydrous magnesium sulfate and concentrated in vacuo. The thus-obtained oily material was dried in vacuo. The powder was reprecipitated with ether-hexane to obtain the substance [19] (65.0 g, yield: 94.5%).

Workup

  1. distillationethanol was distilled off in vacuo
  2. additionWater (300 ml) was added to the aqueous layer, which
  3. washwas then washed twice with ether, and 1 N HCl (150 ml)
  4. customwas at 0° C.
  5. extractionthe mixture was extracted with ethyl acetate (400 ml)
  6. washThe ethyl acetate layer was washed with water
  7. dry with materialdried with anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe thus-obtained oily material was dried in vacuo
  10. customThe powder was reprecipitated with ether-hexane

Sources & evidence

ORD record
ord-f2246ebe22d640a39f47fd38cbbe7af9
Source dataset
uspto-grants-1983_08
Patent number
US04400316

Reaction notes

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