Triphenylphosphine → (Z)-(1S,4R,6S,18R)-18-[2-(4-ethynyl-thiazol-2-yl)-7-methoxy-8-methyl-quinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.4.0.0*4,6*]nonadec-7-ene-4-carboxylic acid methyl ester

HRID 880745Notes

Reaction equation

HRID 880745 reaction equation
[CH3:1][O:2][C:3]([C@@:5]12[CH2:23][C@H:22]1[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17][CH2:16][N:15]([CH3:24])[C:14](=[O:25])[N:13]1[C@@H:8]([CH2:9][C@H:10]([OH:26])[CH2:11][CH2:12]1)[C:7](=[O:27])[NH:6]2)=[O:4].[CH3:28][O:29][C:30]1[C:39]([CH3:40])=[C:38]2[C:33]([C:34](O)=[CH:35][C:36]([C:41]3[S:42][CH:43]=[C:44]([C:46]#[CH:47])[N:45]=3)=[N:37]2)=[CH:32][CH:31]=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>[CH3:1][O:2][C:3]([C@@:5]12[CH2:23][C@H:22]1[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17][CH2:16][N:15]([CH3:24])[C:14](=[O:25])[N:13]1[C@@H:8]([CH2:9][C@H:10]([O:26][C:34]3[C:33]4[C:38](=[C:39]([CH3:40])[C:30]([O:29][CH3:28])=[CH:31][CH:32]=4)[N:37]=[C:36]([C:41]4[S:42][CH:43]=[C:44]([C:46]#[CH:47])[N:45]=4)[CH:35]=3)[CH2:11][CH2:12]1)[C:7](=[O:27])[NH:6]2)=[O:4]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 68495095(Z)-(1S,4R,6S,18R)-18-hydroxy-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.4.0.0*4,6*]nonadec-7-ene-4-carboxylic acid methyl esterHCID 178437374HCID 178437374, compound

Product 1

HCID 87472167(Z)-(1S,4R,6S,18R)-18-[2-(4-ethynyl-thiazol-2-yl)-7-methoxy-8-methyl-quinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.4.0.0*4,6*]nonadec-7-ene-4-carboxylic acid methyl esterYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of compound 36 (0.143 g, 1 eq.), compound 209b (0.112 g, 1 eq.), and polystyrene supported triphenylphosphine (0.411 g, 2 eq.) in anhydrous THF (8 mL) was added dropwise DIAD (150 μL, 2 eq.) at 0° C. The reaction mixture was stirred at room temperature overnight. The mixture was filtered on autocup, washed with dichloromethane, and concentrated. The crude residue was purified by chromatography on a silica gel to give compound 37 in 42% yield. MS (ESI, EI+) m/z=658 (MH+).

Workup

  1. filtrationThe mixture was filtered on autocup
  2. washwashed with dichloromethane
  3. concentrationconcentrated
  4. customThe crude residue was purified by chromatography on a silica gel

Sources & evidence

ORD record
ord-da6e56a8e31748feb6ddcaa67cea348a
Source dataset
uspto-grants-2015_03
Patent number
US08993595B2

Reaction notes

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