Triphenylphosphine → HCID 59738307, compound

HRID 559515Notes

Reaction equation

HRID 559515 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[N:12][NH:13][N:14]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].O[CH2:16][C:17]([CH3:23])([CH3:22])[C:18]([O:20][CH3:21])=[O:19].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[N:12][N:13]([CH2:16][C:17]([CH3:23])([CH3:22])[C:18]([O:20][CH3:21])=[O:19])[N:14]=2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 84152Methyl 3-hydroxypivalateHCID 8589055-[4-(propan-2-yl)phenyl]-1H-1,2,3,4-tetrazoleHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 59738307HCID 59738307, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of crude 5-(4-isopropylphenyl)-2H-tetrazole (1.0 g, ˜5.3 mmol), methyl 3-hydroxy-2,2-dimethylpropanoate (830 mg, 8.0 mmol), and PPh3 (2.1 g, 8.0 mmol) in THF (5 mL) was added DEAD (1.35 mL, 8.0 mmol) dropwise. The reaction mixture was stirred for 2 h. LC/MS indicated the reaction was complete. The reaction mixture was filtered and purified on RP-HPLC using a mixture of acetonitrile and H2O to give methyl 3-(5-(4-isopropylphenyl)-2H-tetrazol-2-yl)-2,2-dimethylpropanoate (480 mg, 32% for two steps). LRMS (M+H+) m/z 303.2.

Workup

  1. filtrationThe reaction mixture was filtered
  2. custompurified on RP-HPLC
  3. additiona mixture of acetonitrile and H2O

Sources & evidence

ORD record
ord-561c98c1374947c7905337e50dba98dc
Source dataset
uspto-grants-2011_11
Patent number
US08063082B2

Reaction notes

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