Potassium Carbonate → HCID 178495700, compound

HRID 1900070Notes

Reaction equation

HRID 1900070 reaction equation
[C:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]2[CH:14]=[CH:13][C:12]([N:15](OCC)[C:16](=[O:18])[OH:17])=[CH:11][CH:10]=2)[CH2:5][CH2:4]1)#[N:2].[CH3:22][O:23][CH2:24][C@H:25]1[CH2:29]OC(=O)O1.C(=O)([O-])[O-].[K+].[K+]>>[CH3:22][O:23][CH2:24][C@@H:25]1[O:17][C:16](=[O:18])[N:15]([C:12]2[CH:11]=[CH:10][C:9]([C@H:6]3[CH2:5][CH2:4][C@H:3]([C:1]#[N:2])[CH2:8][CH2:7]3)=[CH:14][CH:13]=2)[CH2:29]1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 11007941(S)-(-)-4-(Methoxymethyl)-1,3-dioxolan-2-oneHCID 178475116HCID 178475116, compound

Product 1

HCID 178495700HCID 178495700, compound

Procedure

A suspension of 500 mg (1.84 mmol) of trans-[4-(4-cyano-cyclohexyl)-phenyl]-ethoxycarbamic acid, 365 mg (2.8 mmol) of (S)-4-methoxymethyl-1,3-dioxolan-2-one and 185 mg of potassium carbonate was stirred at 160° for 16 hours. The reaction mixture was chromatographed over silica gel with ethyl acetate/hexane 1:1 and the yellow crystals obtained were recrystallized from ethyl acetate. 165 mg (29%) were obtained as white crystals with m.p. 174°.

Workup

  1. customThe reaction mixture was chromatographed over silica gel with ethyl acetate/hexane 1:1
  2. customthe yellow crystals obtained
  3. customwere recrystallized from ethyl acetate
  4. custom165 mg (29%) were obtained as white crystals with m.p. 174°

Sources & evidence

ORD record
ord-be3bbd52ba8849de959395503f0e19cc
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

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