Methanesulfonic Acid → 1,3-Dioxane-4-acetamide, 6-(cyanomethyl)-2,2-dimethyl-N,N-diphenyl-, (4R-cis)-(9CI)

HRID 129942Notes

Reaction equation

HRID 129942 reaction equation
[C:1]([CH2:3][CH:4]([OH:24])[CH2:5][CH:6]([OH:23])[CH2:7][C:8]([N:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9])#[N:2].CO[C:27](OC)([CH3:29])[CH3:28].CS(O)(=O)=O>CC(C)=O>[C:1]([CH2:3][C@H:4]1[O:24][C:27]([CH3:29])([CH3:28])[O:23][C@@H:6]([CH2:7][C:8]([N:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:9])[CH2:5]1)#[N:2]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 64952,2-DimethoxypropaneHCID 224153406-cyano-3,5-dihydroxy-N,N-diphenylhexanamide

Product 1

HCID 108830131,3-Dioxane-4-acetamide, 6-(cyanomethyl)-2,2-dimethyl-N,N-diphenyl-, (4R-cis)-(9CI)

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Crude [R-(R*,R*)]-6-cyano-3,5-dihydroxy-N,N-diphenylhexanamide, approximately 0.18 mol, is dissolved in 2,2-dimethoxypropane (160 mL, 1.5 mol) and acetone (300 mL). Methanesulfonic acid (0.5 mL) is added, and the solution is stirred for 2 hours at room temperature. The reaction is quenched by the addition of aqueous sodium bicarbonate (800 mL) and ethyl acetate (500 mL). The ethyl acetate solution is concentrated by vacuum distillation to give 62.5 g of (4R -cis)-6-(cyanomethyl)-2,2-dimethyl-N,N-diphenyl-1,3-dioxane-4-acetamide as an off-white crystalline solid (mp 98°-100° C., uncorrected).

Workup

  1. customThe reaction is quenched by the addition of aqueous sodium bicarbonate (800 mL) and ethyl acetate (500 mL)
  2. concentrationThe ethyl acetate solution is concentrated by vacuum distillation

Sources & evidence

ORD record
ord-c750e7bb9385468bb3c91ae7f37983df
Source dataset
uspto-grants-1995_11
Patent number
US05470981

Reaction notes

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