p-Toluenesulfonic acid → HCID 89962762, compound

HRID 337932Notes

Reaction equation

HRID 337932 reaction equation
[CH3:1][N:2]1[C:6]([C@@:7]2([OH:14])[CH2:12][CH2:11][CH2:10][CH2:9][C@@H:8]2O)=[CH:5][CH:4]=[N:3]1.C(OC)(OC)(OC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Br-].[Li+].C(Br)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.C(#N)C.ClCCl>[CH3:1][N:2]1[C:6]([C@:7]23[O:14][C@H:8]2[CH2:9][CH2:10][CH2:11][CH2:12]3)=[CH:5][CH:4]=[N:3]1

Participants

10

Reactant 6

HCID 6101p-Toluenesulfonic acidHCID 10482Acetyl bromideHCID 11430Potassium CarbonateHCID 15050Trimethyl orthoacetateHCID 82050Lithium BromideHCID 89962992HCID 89962992, compound

Product 1

HCID 89962762HCID 89962762, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

The reaction and aftertreatment were conducted in the same manner as in Example 102b by using the (1S,2S)-1-(1-methyl-1H-pyrazol-5-yl)cyclohexane-1,2-diol (423 mg, 2.15 mmol) prepared in Example 123c, trimethyl orthoacetate (0.688 mL, 5.38 mmol), p-toluenesulfonic acid (20.5 mg, 0.11 mmol), dichloromethane (6.0 mL), acetonitrile (6.0 mL), lithium bromide (466 mg, 5.38 mmol), acetyl bromide (0.398 mL, 5.38 mmol), methanol (6.0 mL) and potassium carbonate (743 mg, 5.38 mmol), to yield the title compound (180 mg, 47%).

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-19940323e27746af8df8bcae34636e0c
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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