tert-butyl 4-{3-[(3R)-3-({(1S)-3-tert-butoxy-1-[5-(2-fluoroethoxy)pyridin-3-yl]-3-oxopropyl}carbamoyl)piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylat → (3S)-3-[5-(2-fluoroethoxy)pyridin-3-yl]-3-[({(3R)-1-[3-(piperidin-4-yl)propanoyl]piperidin-3-yl}carbonyl)amino]propanoic acid

HRID 526321Notes

Reaction equation

HRID 526321 reaction equation
C([O:5][C:6](=[O:45])[CH2:7][C@H:8]([NH:19][C:20]([C@@H:22]1[CH2:27][CH2:26][CH2:25][N:24]([C:28](=[O:44])[CH2:29][CH2:30][CH:31]2[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33][CH2:32]2)[CH2:23]1)=[O:21])[C:9]1[CH:10]=[N:11][CH:12]=[C:13]([O:15][CH2:16][CH2:17][F:18])[CH:14]=1)(C)(C)C>C(O)=O>[F:18][CH2:17][CH2:16][O:15][C:13]1[CH:14]=[C:9]([C@@H:8]([NH:19][C:20]([C@@H:22]2[CH2:27][CH2:26][CH2:25][N:24]([C:28](=[O:44])[CH2:29][CH2:30][CH:31]3[CH2:32][CH2:33][NH:34][CH2:35][CH2:36]3)[CH2:23]2)=[O:21])[CH2:7][C:6]([OH:45])=[O:5])[CH:10]=[N:11][CH:12]=1

Participants

3

Reactant 1

HCID 71609266tert-butyl 4-{3-[(3R)-3-({(1S)-3-tert-butoxy-1-[5-(2-fluoroethoxy)pyridin-3-yl]-3-oxopropyl}carbamoyl)piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylat

Product 1

HCID 71609419(3S)-3-[5-(2-fluoroethoxy)pyridin-3-yl]-3-[({(3R)-1-[3-(piperidin-4-yl)propanoyl]piperidin-3-yl}carbonyl)amino]propanoic acidYield 61.3%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Tert-butyl 4-{3-[(3R)-3-({(1S)-3-tert-butoxy-1-[5-(2-fluoroethoxy)pyridin-3-yl]-3-oxopropyl}carbamoyl)piperidin-1-yl]-3-oxopropyl}piperidine-1-carboxylat (660 mg, 1.06 mmol) in formic acid (12 mL) was heated for 30 minutes to 60° C. and 10 minutes to 100° C. The solution was concentrated under reduced pressure and the residue was purified by preparative HPLC to yield 311 mg of (3S)-3-[5-(2-fluoroethoxy)pyridin-3-yl]-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-079ab902a805412c8f3383370045ba9c
Source dataset
uspto-grants-2016_05
Patent number
US09345793B2

Reaction notes

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