Hydrochloric Acid → HCID 86757996, compound

HRID 843749Notes

Reaction equation

HRID 843749 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16]([N:18]2[CH2:23][CH2:22][CH2:21][C@@H:20](C(N[C@H](C#C)CC(O)=O)=O)[CH2:19]2)=[O:17])[CH2:10][CH2:9]1.Cl.[CH2:35]([OH:37])[CH3:36]>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:35]([O:37][C:3](=[O:5])[CH2:2][C@@H:9]([C:10]#[CH:11])[NH:8][C@@H:20]1[CH2:21][CH2:22][CH2:23][N:18]([C:16](=[O:17])[CH2:15][CH2:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH2:19]1)[CH3:36]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 86757992HCID 86757992, compound

Product 1

HCID 86757996HCID 86757996, compound

Procedure

A mixture of N-[(R)-1-{3-(4-piperidyl)propionyl}-3-piperidylcarbonyl]-3(S)-ethynyl-β-alanine trifluoroacetate (0.57 g) and 4.9 HCl in ethanol (30 ml) was stirred at ambient temperature for 2 hours, and the mixture was evaporated in vacuo. The residue was purified by HPLc on C18 silica gel eluting with a solution of 18% CH3CN in 0.1% aqueous TFA solution, and the fractions containing object compound were combined and evaporated in vacuo and freeze-dried to give N-[(R)-1-{3-(4-piperidyl)propionyl}-3-piperidyl]-3(S)-ethynyl-β-alanine ethyl ester trifluoro acetate (0.52 g).

Workup

  1. customthe mixture was evaporated in vacuo
  2. customThe residue was purified by HPLc on C18 silica gel eluting with a solution of 18% CH3CN in 0.1% aqueous TFA solution
  3. additionthe fractions containing object compound
  4. customevaporated in vacuo
  5. customfreeze-dried

Sources & evidence

ORD record
ord-61d1835c1a914fcfb40bbbc35afad59b
Source dataset
uspto-grants-2002_04
Patent number
US06380215B1

Reaction notes

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