Ethanol → HCID 54074795, compound

HRID 267152Notes

Reaction equation

HRID 267152 reaction equation
ClC(C[C@@H](O)C)C[C@@H:4]([NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1.[OH-].[K+].[CH2:33]([OH:35])[CH3:34]>>[CH2:19]([O:18][C:17]([NH:16][C@@H:4]([CH2:5][C:6]1[CH:7]=[CH:8][C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=1)[C@@H:34]1[O:35][CH2:33]1)=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 14797Potassium HydroxideHCID 86751127HCID 86751127, compound

Product 1

HCID 54074795HCID 54074795, compound

Procedure

1.02 g of benzyl [3-chloro-2(S)-hydroxypropyl-1(S)-[(2-naphthyl)methyl]propyl]carbamate were stirred in 40 ml of ethanol with 4 ml of 0.7M potassium hydroxide solution in ethanol for 0.75 hours. The solvent was removed by evaporation and the residue was partitioned between dichloromethane and water. The organic phase was dried over anhydrous sodium sulphate and evaporated to give a white solid which was recrystallized from ethyl acetate/n-hexane. There was obtained 0.879 g of 3(S)-(benzyloxyformamido)-1,2(S)-epoxy-4-(2-naphthyl)butane as a white solid of melting point 115°-116° C.

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue was partitioned between dichloromethane and water
  3. dry with materialThe organic phase was dried over anhydrous sodium sulphate
  4. customevaporated
  5. customto give a white solid which
  6. customwas recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-db9636b86efe48e984757fcd0c8a5740
Source dataset
uspto-grants-1997_07
Patent number
US05652369

Reaction notes

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