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

HRID 488101Notes

Reaction equation

HRID 488101 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-7c46910e63f04b74b357cc650e8a6e79
Source dataset
uspto-grants-1994_03
Patent number
US05298627

Reaction notes

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