Triphenylphosphine → N-Cbz-{4-[7-methoxy-8-methyl-2-(4-trifluoromethyl-thiazol-2-yl)-quinolin-4-yloxy]}-piperidine-2-carboxylic acid methyl ester

HRID 880735Notes

Reaction equation

HRID 880735 reaction equation
[CH3:1][O:2][C:3]1[C:12]([CH3:13])=[C:11]2[C:6]([C:7]([OH:23])=[CH:8][C:9]([C:14]3[S:15][CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[N:18]=3)=[N:10]2)=[CH:5][CH:4]=1.O[C@@H:25]1[CH2:30][CH2:29][N:28]([C:31]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:32])[C@H:27]([C:41]([O:43][CH3:44])=[O:42])[CH2:26]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:44][O:43][C:41]([CH:27]1[CH2:26][CH:25]([O:23][C:7]2[C:6]3[C:11](=[C:12]([CH3:13])[C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[N:10]=[C:9]([C:14]3[S:15][CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[N:18]=3)[CH:8]=2)[CH2:30][CH2:29][N:28]1[C:31]([O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:32])=[O:42]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 14890235cis-4-Hydroxy-piperidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl esterHCID 178487696HCID 178487696, compound

Product 1

HCID 66730320N-Cbz-{4-[7-methoxy-8-methyl-2-(4-trifluoromethyl-thiazol-2-yl)-quinolin-4-yloxy]}-piperidine-2-carboxylic acid methyl esterYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of compounds 203b (1 g, 1 eq.) and 12 (1.39 g, 1.2 eq.), and triphenylphosphine (1.34 g, 1.5 eq.) in anhydrous THF (40 mL) at 0° C. was added DIAD (1.02 mL, 1.5 eq.). The reaction mixture was stirred at room temperature for 2 hrs. THF was then removed under reduced pressure and the residue was purified by chromatography on silica gel (petroleum ether/EtOAc) to yield compound 13 as a white solid in 52% yield. MS (ESI, EI+) m/z=616 (MH+).

Workup

  1. customTHF was then removed under reduced pressure
  2. customthe residue was purified by chromatography on silica gel (petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-97f421a7962b4a3983f1c93e3eeeef53
Source dataset
uspto-grants-2015_03
Patent number
US08993595B2

Reaction notes

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