Hydrochloric Acid → 3-({[(3R)-1-{3-[1-(tert-butoxycarbonyl)piperidin-4-yl]propanoyl}piperidin-3-yl]carbonyl}amino)-3-[4-(2-fluoroethoxy)phenyl]propanoic acid

HRID 526319Notes

Reaction equation

HRID 526319 reaction equation
[F:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([NH:17][C:18]([C@@H:20]2[CH2:25][CH2:24][CH2:23][N:22]([C:26](=[O:42])[CH2:27][CH2:28][CH:29]3[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]3)[CH2:21]2)=[O:19])[CH2:12][C:13]([O:15]C)=[O:14])=[CH:7][CH:6]=1.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].Cl>CO.O>[C:38]([O:37][C:35]([N:32]1[CH2:31][CH2:30][CH:29]([CH2:28][CH2:27][C:26]([N:22]2[CH2:23][CH2:24][CH2:25][C@@H:20]([C:18]([NH:17][CH:11]([C:8]3[CH:7]=[CH:6][C:5]([O:4][CH2:3][CH2:2][F:1])=[CH:10][CH:9]=3)[CH2:12][C:13]([OH:15])=[O:14])=[O:19])[CH2:21]2)=[O:42])[CH2:34][CH2:33]1)=[O:36])([CH3:41])([CH3:40])[CH3:39]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 17749109Barium hydroxide, octahydrateHCID 89407580tert-butyl 4-{3-[(3R)-3-({1-[4-(2-fluoroethoxy)phenyl]-3-methoxy-3-oxopropyl}carbamoyl)piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate

Product 1

HCID 716092653-({[(3R)-1-{3-[1-(tert-butoxycarbonyl)piperidin-4-yl]propanoyl}piperidin-3-yl]carbonyl}amino)-3-[4-(2-fluoroethoxy)phenyl]propanoic acidYield 100.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

96 mg (0.16 mmol) tert-butyl 4-{3-[(3R)-3-({1-[4-(2-fluoroethoxy)phenyl]-3-methoxy-3-oxopropyl}carbamoyl)piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylate were dissolved in 20 ml methanol. 512 mg (1.62 mmol) barium hydroxide octahydrate were added. The mixture was stirred at room temperature for 70 hours and then diluted with 20 ml water. The mixture was acidified with 1 N hydrochloric acid to pH 4 and extracted with 2×40 ml dichloromethane. Concentration of the organic phase gave 93 mg (99%) 3-({[(3R)-1-{3-[1-(tert-butoxycarbonyl)piperidin-4-yl]propanoyl}piperidin-3-yl]carbonyl}amino)-3-[4-(2-fluoroethoxy)phenyl]propanoic acid.

Workup

  1. extractionextracted with 2×40 ml dichloromethane

Sources & evidence

ORD record
ord-0293f831a2fb47109a10f11035d1583d
Source dataset
uspto-grants-2016_05
Patent number
US09345793B2

Reaction notes

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