Hydrochloric Acid → 3(S)-(5,6,7,8-Tetrahydro-quinolin-3-yl)-3-(5-(5,6,7,8-tetrahydro-[1,8]-naphthyridin-2-yl)-pentanoylamino)-propionic acid trifluoroacetate

HRID 1837878Notes

Reaction equation

HRID 1837878 reaction equation
[N:1]1[C:10]2[NH:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([NH:17][C@H:18]([C:25]1[CH:26]=[N:27][C:28]2[C:33]([CH:34]=1)=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:19][C:20]([O:22]CC)=[O:21])=[O:16].CCO.[Li+].[OH-].Cl.[C:41]([OH:47])([C:43]([F:46])([F:45])[F:44])=[O:42]>O=[Pt]=O>[F:44][C:43]([F:46])([F:45])[C:41]([OH:47])=[O:42].[N:27]1[C:28]2[CH2:29][CH2:30][CH2:31][CH2:32][C:33]=2[CH:34]=[C:25]([C@@H:18]([NH:17][C:15](=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][C:2]2[CH:3]=[CH:4][C:5]3[CH2:6][CH2:7][CH2:8][NH:9][C:10]=3[N:1]=2)[CH2:19][C:20]([OH:22])=[O:21])[CH:26]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 60105751Ethyl 3-(5-(5,6,7,8-tetrahydro-[1,8]-naphthyridin-2-yl)pentanoylamino)-3(S)-(quinolin-3-yl)-propionate

Product 1

HCID 697760313(S)-(5,6,7,8-Tetrahydro-quinolin-3-yl)-3-(5-(5,6,7,8-tetrahydro-[1,8]-naphthyridin-2-yl)-pentanoylamino)-propionic acid trifluoroacetate

Reagents, catalysts & solvents 1

HCID 345198Adams' catalystCatalyst

Procedure

A mixture of 5-8 (0.1 g, 0.3 mmol) and PtO2 (0.04 g) in 10 mL TFA was purged with argon 3 times under vacuum, and treated under balloon hydrogenation condition for 18 hr. It was then filtered through a celite pad. The solution was concentrated. EtOH (3 mL) and LiOH (1 mL, 1 M, 1 mmol) were added. After stirring for 3 hr, the reaction mixture was treated with 2N HCl (2 mL), concentrated and purified by reverse phase HPLC (C18 column; gradient: H2O/CH3CN/TFA from 95:5:0.1 to 5:95:0.1 over 45 min) to give the desired product 5-10 as the TFA salt.

Workup

  1. customwas purged with argon 3 times under vacuum
  2. additiontreated under balloon hydrogenation condition for 18 hr
  3. filtrationIt was then filtered through a celite pad
  4. concentrationThe solution was concentrated
  5. concentrationconcentrated
  6. custompurified by reverse phase HPLC (C18 column; gradient: H2O/CH3CN/TFA from 95:5:0.1 to 5:95:0.1 over 45 min)

Sources & evidence

ORD record
ord-0df887a625a743b8a43097823e768cd8
Source dataset
uspto-grants-2004_08
Patent number
US06784190B2

Reaction notes

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