Hydrochloric Acid → HCID 178427550, compound

HRID 435396Notes

Reaction equation

HRID 435396 reaction equation
[NH:1]([C:69]([O:71][C:72]([CH3:75])([CH3:74])[CH3:73])=[O:70])[C@H:2]([C:12]([NH:14][C@H:15]([C:33]([NH:35][C@H:36]([C:41]([N:43]1[CH2:68][CH2:67][CH2:66][C@H:44]1[C:45]([NH:47][CH2:48][C:49]([N:51]1[CH2:65][CH2:64][CH2:63][C@H:52]1[C:53]([O:55]CC1C=CC=CC=1)=[O:54])=[O:50])=[O:46])=[O:42])[CH2:37][CH:38]([CH3:40])[CH3:39])=[O:34])[CH2:16][CH2:17][CH2:18][NH:19][C:20](=[NH:32])[NH:21][S:22]([C:25]1[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=1)(=[O:24])=[O:23])=[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.CCOCC>CO>[NH:1]([C:69]([O:71][C:72]([CH3:74])([CH3:73])[CH3:75])=[O:70])[C@H:2]([C:12]([NH:14][C@H:15]([C:33]([NH:35][C@H:36]([C:41]([N:43]1[CH2:68][CH2:67][CH2:66][C@H:44]1[C:45]([NH:47][CH2:48][C:49]([N:51]1[CH2:65][CH2:64][CH2:63][C@H:52]1[C:53]([OH:55])=[O:54])=[O:50])=[O:46])=[O:42])[CH2:37][CH:38]([CH3:39])[CH3:40])=[O:34])[CH2:16][CH2:17][CH2:18][NH:19][C:20](=[NH:32])[NH:21][S:22]([C:25]1[CH:26]=[CH:27][C:28]([CH3:29])=[CH:30][CH:31]=1)(=[O:24])=[O:23])=[O:13])[CH2:3][O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium Hydroxide2×HCID 178427551HCID 178427551, compound

Product 1

HCID 178427550HCID 178427550, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The substance [14] (105.44 g, 97.43 mM) was dissolved in methanol (350 ml). 1 N NaOH (125.36 ml, 1.3 molar excess) was added dropwise with ice cooling and the mixture was stirred at room temperature for 2 hours. 1 N NaOH (20 ml) was added to the reaction mixture, which was then stirred at room temperature for 1.5 hours. 1 N HCl (49 ml) was added to the reaction mixture to adjust the same to pH 6 and the methanol was distilled off in vacuo. Water was added to the aqueous layer, which was then washed with ether (100 ml). 1 N HCl (50 ml) was added dropwise with ice cooling to the aqueous layer. As the stirring became impossible due to the formation of a precipitate of viscous material, ethyl acetate (300 ml) was added and 1 N HCl (60 ml) was added dropwise to adjust the pH of the aqueous layer to pH 2. The aqueous layer was extracted with ethyl acetate (1 l. and 500 ml), and washed twice with saturated sodium chloride solution and water. After drying with anhydrous sodium sulfate, the ethyl acetate layer was concentrated in vacuo to obtain an oily material which was solidified by adding ether. Recrystallization was effected from ethyl acetate-ether to obtain the substance [15] (95.12 g, yield: 100%).

Workup

  1. stirringwas then stirred at room temperature for 1.5 hours
  2. distillationthe methanol was distilled off in vacuo
  3. additionWater was added to the aqueous layer, which
  4. washwas then washed with ether (100 ml)
  5. addition1 N HCl (50 ml) was added dropwise with ice cooling to the aqueous layer
  6. additionwas added
  7. addition1 N HCl (60 ml) was added dropwise
  8. extractionThe aqueous layer was extracted with ethyl acetate (1 l. and 500 ml)
  9. washwashed twice with saturated sodium chloride solution and water
  10. dry with materialAfter drying with anhydrous sodium sulfate
  11. concentrationthe ethyl acetate layer was concentrated in vacuo
  12. customto obtain an oily material which
  13. customRecrystallization

Sources & evidence

ORD record
ord-f82c0f7d04404e96912b0ca98ae70b11
Source dataset
uspto-grants-1983_08
Patent number
US04400316

Reaction notes

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