Triethylamine → HCID 57544846, compound

HRID 1254404Notes

Reaction equation

HRID 1254404 reaction equation
OC(C(F)(F)F)=O.[F:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=2)=[C:13]([C@:22]([C@@H:30]2[CH2:35][CH2:34][CH2:33][NH:32][CH2:31]2)([OH:29])[CH2:23][CH2:24][CH2:25][CH2:26][O:27][CH3:28])[CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C.[N+](C1C=CC([O:50][C:51]([NH:53][C@H:54]2[CH2:59][CH2:58][CH2:57][N:56]([C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])[CH2:55]2)=O)=CC=1)([O-])=O>C(Cl)Cl>[F:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=2)=[C:13]([C@:22]([C@@H:30]2[CH2:35][CH2:34][CH2:33][N:32]([C:51]([NH:53][C@H:54]3[CH2:59][CH2:58][CH2:57][N:56]([C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])[CH2:55]3)=[O:50])[CH2:31]2)([OH:29])[CH2:23][CH2:24][CH2:25][CH2:26][O:27][CH3:28])[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 57544763HCID 57544763, compoundHCID 86626204HCID 86626204, compound

Product 1

HCID 57544846HCID 57544846, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-1-(6-fluoro-3′-methylbiphenyl-2-yl)-5-methoxy-1-((R)-piperidin-3-yl)pentan-1-ol TFA salt (62.7 mg, 0.13 mmol) in anhydrous CH2Cl2 (0.5 mL) containing triethyl amine (0.1 mL) was added to above solution of (S)-tert-butyl 3-((4-nitrophenoxy)carbonylamino)piperidine-1-carboxylate within 1 min. The mixture was stirred for 30 min. The reaction mixture was evaporated and the residue was purified by preparative HPLC to afford (S)-tert-Butyl 3-((R)-3-((S)-1-(6-fluoro-3′-methylbiphenyl-2-yl)-1-hydroxy-5-methoxypentyl)piperidine-1-carboxamido)piperidine-1-carboxylate (35 mg). MS m/z 612 (M+H)+.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-9a0bc9eb7fdf4f5fb42fe63e666da67f
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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