Triphenylphosphine → Methyl(+/-)-4-[4-[2-(6-Methylaminopyridin-2-yl)-1-ethoxy]phenyl]-3-(5-methylthiazol2-yl)butanoate

HRID 1816014Notes

Reaction equation

HRID 1816014 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[OH:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([C:29]2[S:30][C:31]([CH3:34])=[CH:32][N:33]=2)[CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:18][CH:17]=1.[CH3:35][NH:36][C:37]1[N:42]=[C:41]([CH:43](O)[CH3:44])[CH:40]=[CH:39][CH:38]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CC(OC)(C)C>[CH3:35][NH:36][C:37]1[N:42]=[C:41]([CH2:43][CH2:44][O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([C:29]3[S:30][C:31]([CH3:34])=[CH:32][N:33]=3)[CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:18][CH:17]=2)[CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 20775669Methyl I(2)-[(4-hydroxyphenyl)methyl]-5-methyl-2-thiazolepropanoateHCID 223194656-(Methylamino)-2-pyridylethanol

Product 1

HCID 22496022Methyl(+/-)-4-[4-[2-(6-Methylaminopyridin-2-yl)-1-ethoxy]phenyl]-3-(5-methylthiazol2-yl)butanoateYield 106.4%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

Diisopropyl azodicarboxylate (0.25 mL, 1.28 mmole) was added to a suspension of methyl (±)-4-(4-hydroxyphenyl)-3-(5-methylthiazol-2-yl)butanoate (249 mg, 0.85 mmole), 6-(methylamino)-2-pyridylethanol (194 mg, 1.28 mmole), and triphenylphosphine (336 mg, 1.28 mmole) in TBME (5 mL) at 0° C. The mixture was allowed to warm to RT as the bath warmed. After 72 hr the mixture was concentrated and the residue was chromatographed on silica gel (30% EtOAc/CHCl3). Fractions containing the product were concentrated to give the title compound (385 mg, contaminated with triphenylphosphine oxide): MS (ES) m/e 426 (M+H)+.

Workup

  1. temperaturewarmed
  2. concentrationAfter 72 hr the mixture was concentrated
  3. customthe residue was chromatographed on silica gel (30% EtOAc/CHCl3)
  4. additionFractions containing the product
  5. concentrationwere concentrated

Sources & evidence

ORD record
ord-f421b1fa64c64b5888d1534b933a8a7e
Source dataset
uspto-grants-2005_04
Patent number
US06881736B1

Reaction notes

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