Hydrochloric Acid → HCID 86598027, compound

HRID 751750Notes

Reaction equation

HRID 751750 reaction equation
[N:1]1(C(OC(C)(C)C)=O)[CH2:5][CH2:4][CH2:3][C@H:2]1[C:6]([O:8][CH2:9][C@H:10]([NH:23][C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])[C:11]([O:13][CH2:14][C:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:12])=[O:7].[ClH:41]>O1CCOCC1>[Cl-:41].[CH2:27]([O:26][C:24]([NH:23][C@H:10]([C:11]([O:13][CH2:14][C:15](=[O:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:12])[CH2:9][O:8][C:6]([C@@H:2]1[CH2:3][CH2:4][CH2:5][NH2+:1]1)=[O:7])=[O:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59753406HCID 59753406, compound

Product 1

HCID 86598027HCID 86598027, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

31.5 g (56.8 mmol) of the compound from example 2A are dissolved in 200 ml of 4M hydrogen chloride solution in dioxane under argon and stirred overnight at RT. The reaction solution is concentrated, and taken up once using ethyl acetate and concentrated again, and concentrated twice using dichloromethane. The residue is dissolved in ethanol (100 ml), diethyl ether (400 ml) is slowly added with stirring, the mixture is cooled and the precipitate is filtered off with suction. 25.2 g (86% of th.) of the product are obtained, which is reacted further without further purification.

Workup

  1. concentrationThe reaction solution is concentrated
  2. concentrationconcentrated again
  3. concentrationconcentrated twice using dichloromethane
  4. dissolutionThe residue is dissolved in ethanol (100 ml)
  5. additiondiethyl ether (400 ml) is slowly added
  6. stirringwith stirring
  7. temperaturethe mixture is cooled
  8. filtrationthe precipitate is filtered off with suction
  9. custom25.2 g (86% of th.) of the product are obtained
  10. customwhich is reacted further without further purification

Sources & evidence

ORD record
ord-acd18fa8aa3d49c1af67a15f50a75104
Source dataset
uspto-grants-2008_07
Patent number
US07405201B2

Reaction notes

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