Hydrochloric Acid → HCID 89407542, compound

HRID 526315Notes

Reaction equation

HRID 526315 reaction equation
C(OC([N: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:24]([NH:26][CH:27]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH2:39][CH2:40][F:41])[CH:33]=3)[CH2:28][C:29]([OH:31])=[O:30])=[O:25])[CH2:19]2)=[O:17])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[F:41][CH2:40][CH2:39][O:38][C:34]1[CH:35]=[CH:36][CH:37]=[C:32]([C@@H:27]([NH:26][C:24]([C@@H:20]2[CH2:21][CH2:22][CH2:23][N:18]([C:16](=[O:17])[CH2:15][CH2:14][CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[CH2:19]2)=[O:25])[CH2:28][C:29]([OH:31])=[O:30])[CH:33]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71609227HCID 71609227, compound

Product 1

HCID 89407542HCID 89407542, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To 3-({[(3R)-1-{3-[1-(tert-butoxycarbonyl)piperidin-4-yl]propanoyl}piperidin-3-yl]carbonyl}amino)-3-[3-(2-fluoroethoxy)phenyl]propanoic acid (65 mg, 90 μmol) in dioxane was added a 4 M solution of hydrochloric acid in dioxane (0.23 ml, 900 μmol) and stirred for 3 hours at room temperature. The solution was concentrated under reduced pressure and the residue was purified by preparative HPLC to yield 8.7 mg of (3S)-3-[5-(2-fluoroethoxy)phenyl]-3-[({(3R)-1-[3-(piperidin-4-yl)propanoyl]piperidin-3-yl}carbonyl)amino]propanoic acid.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-8e09c35835b24e3594608eddc3827e45
Source dataset
uspto-grants-2016_05
Patent number
US09345793B2

Reaction notes

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