Tributylphosphine → HCID 54491673, compound

HRID 1419702Notes

Reaction equation

HRID 1419702 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]([C:15]([N:17]([C@H:21]([CH3:38])[C@:22]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=3[F:37])([OH:29])[CH2:23][N:24]3[CH:28]=[N:27][CH:26]=[N:25]3)[CH2:18][CH2:19]O)=[O:16])=[C:12]([CH3:14])[N:13]=2)=[CH:5][CH:4]=1)#[N:2].C(P(CCCC)CCCC)CCC>C1COCC1>[F:37][C:31]1[CH:32]=[C:33]([F:36])[CH:34]=[CH:35][C:30]=1[C@:22]1([CH2:23][N:24]2[CH:28]=[N:27][CH:26]=[N:25]2)[O:29][CH2:19][CH2:18][N:17]([C:15]([C:11]2[S:10][C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=3)=[N:13][C:12]=2[CH3:14])=[O:16])[C@@H:21]1[CH3:38]

Participants

4

Reactant 2

HCID 13831TributylphosphineHCID 54141090HCID 54141090, compound

Product 1

HCID 54491673HCID 54491673, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A cooled (0° C.) solution of (1R,2R)-2-(4-cyanophenyl)-N-[2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-N-(2-hydroxyethyl)-4-methylthiazole-5-carboxamide (0.45 g, 0.83 mmol, obtained in example 82) in THF (10 mL) was treated with diethylazadicarboxylate (0.20 mL, 1.25 mmol) and tributylphosphine (0.31 mL, 1.25 mmol) for 20 h at room temperature. The mixture was evaporated to dryness and the residue was purified by flash chromatography to give the title compound as a white solid: mp 150°-160° C.; 1H NMR (300 MHz, CDCl3) δ (TMS) 8.06 (d, J=8.4, 2H, arom), 7.76 (s, 1H, triazole), 7.76 (d, J=8.4, 2H, arom), 7.30 (s, 1H, triazole), 7.4-7.2 (m, 1H, arom), 7-6.7 (m, 2H, arom), 5.53 (br), 5.17 (d, J=15.1, 1H, TrCH(H)), 4.7 (br d, 1H), 4.6-4.4 (m, 1H), 4.0 (br d), 3.6 (br s), 2.57 (s, 3H, Me-thiazole), 1.13 (d, J=6.8, 3H, MECH); GC--MS 293 (M+ -acyl, C14H15N4F2O), 227 (acyl group, C12H7N2OS); [α]D =-80.5° (c 1, CHCl3).

Workup

  1. customThe mixture was evaporated to dryness
  2. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-21f6f09bd0b74c73b4b125b189d08c69
Source dataset
uspto-grants-1999_03
Patent number
US05888941

Reaction notes

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