Triphenylphosphine → HCID 118555060, compound

HRID 1051299Notes

Reaction equation

HRID 1051299 reaction equation
[CH3:1][CH:2]([CH2:5][OH:6])[CH2:3][OH:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.O[C:39]1[CH:44]=[CH:43][C:42]([C:45]2[S:46][C:47]([C:51]([O:53][CH2:54][CH3:55])=[O:52])=[C:48]([CH3:50])[N:49]=2)=[CH:41][C:40]=1[N:56]1[CH:60]=[N:59][N:58]=[N:57]1>O1CCCC1.O.C1(C)C=CC=CC=1>[OH:4][CH2:3][CH:2]([CH3:1])[CH2:5][O:6][C:39]1[CH:44]=[CH:43][C:42]([C:45]2[S:46][C:47]([C:51]([O:53][CH2:54][CH3:55])=[O:52])=[C:48]([CH3:50])[N:49]=2)=[CH:41][C:40]=1[N:56]1[CH:60]=[N:59][N:58]=[N:57]1

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 75103MethylpropanediolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 136969441HCID 136969441, compound

Product 1

HCID 118555060HCID 118555060, compoundYield 168%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution was prepared by dissolving 13.5 mg of 2-methypropan-1,3-diol in 1 mL of tetrahydrofuran and adding 39.3 mg of triphenylphosphine and 65 μL of a 40% toluene solution of diethyl azodicarboxylate to the mixture. After stirring the resultant solution at room temperature for 30 minutes, a reaction mixture solution prepared by adding 33.1 mg of ethyl 2-[4-hydroxy-3-(1H-1,2,3,4-tetrazol-1-yl)phenyl]-4-methyl-1,3-thiazole-5-carboxylate to the solution was stirred at room temperature for 3 hours. After the addition of water to the reaction mixture solution, extraction was performed using ethyl acetate. The organic layer was washed with saline and then dried and concentrated under reduced pressure, followed by purifying by a conventional method to obtain 67.7 mg of ethyl 2-[4-(3-hydroxy-2-methylpropoxy)-3-(1H-1,2,3,4-tetrazol-1-yl)phenyl]-4-methyl-1,3-thiazole-5-carboxylate.

Workup

  1. customA solution was prepared
  2. customa reaction mixture solution prepared
  3. extractionto the reaction mixture solution, extraction
  4. washThe organic layer was washed with saline
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customby purifying by a conventional method

Sources & evidence

ORD record
ord-cea7e93bee6d44e0a8a5fbc6819f4e4b
Source dataset
uspto-grants-2016_07
Patent number
US09388174B2

Reaction notes

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