Piperidin-4-ol → HCID 53769526, compound

HRID 651138Notes

Reaction equation

HRID 651138 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[C:8]([NH:15][C@H:16]([C:25](O)=[O:26])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1)([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]>C(OCC)(=O)C>[C:11]([O:10][C:8](=[O:9])[NH:15][C@@H:16]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1)[C:25]([N:5]1[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]1)=[O:26])([CH3:14])([CH3:12])[CH3:13]

Participants

4

Reactant 2

HCID 79341Piperidin-4-olHCID 117439L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl-

Product 1

HCID 53769526HCID 53769526, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Hydroxypiperidine (3.9 mmol) and Boc-L-tyrosine (3.7 mmol) were coupled according to Procedure A (0-25° C. reaction temperature, 60 hour reaction time) with the following workup: the reaction mixture was diluted with ethyl acetate and washed once with base, the base layer was acidified with 2 N HCl and extracted three times with chloroform, and the chloroform extracts concentrated. The resulting foam was purified by chromatography on silica gel eluted with 1-8% ethanol in dichloromethane containing 0.5% NH4OH. Yield 550 mg, 41%; HPLC (40/60) 5.02 minutes (87%).

Workup

  1. washwashed once with base
  2. extractionextracted three times with chloroform
  3. concentrationthe chloroform extracts concentrated
  4. customThe resulting foam was purified by chromatography on silica gel
  5. washeluted with 1-8% ethanol in dichloromethane containing 0.5% NH4OH
  6. customHPLC (40/60) 5.02 minutes (87%)

Sources & evidence

ORD record
ord-3b36dc12d30444dca269024aac247c08
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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