Sulfuric Acid → 2(S)-[2-phenyl-1(S)-phthalimidoethyl]oxirane

HRID 1684697Notes

Reaction equation

HRID 1684697 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C@@H:12]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C@H:13]([OH:20])[CH2:14]OS(C)(=O)=O.[Cl-].[Na+].S(=O)(=O)(O)O>O1CCCC1>[C:22]1([CH2:21][C@@H:12]([C@H:13]2[CH2:14][O:20]2)[N:3]2[C:4](=[O:11])[C:5]3=[CH:6][CH:7]=[CH:8][CH:9]=[C:10]3[C:2]2=[O:1])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 56626679methanesulfonic acid (2S,3S)-3-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-2-hydroxy-4-phenylbutyl ester

Product 1

HCID 102663882(S)-[2-phenyl-1(S)-phthalimidoethyl]oxiraneYield 61.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.26 g of methanesulfonic acid (2S,3S)-3-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-2-hydroxy-4-phenylbutyl ester in 1.6 ml of tetrahydrofuran is treated at -15° with a solution of 0.090 g of potassium tertbutylate in 0.5 ml of tetrahydrofuran and the mixture is stirred for 0.5 hours. The mixture is treated with 2.2 ml of semi-saturated sodium chloride solution and the pH value is adjusted to 6 with 0.1 ml of 1N sulphuric acid. Thereafter, the mixture is extracted with ethyl acetate. The extracts are dried and filtered, and the filtrate is evaporated to give 0.12 g (60%) of 2(S)-[2-phenyl-1(S)-phthalimidoethyl]oxirane, IR (KBr): 1773m and 1709s (C=O of imide).

Workup

  1. extractionThereafter, the mixture is extracted with ethyl acetate
  2. customThe extracts are dried
  3. filtrationfiltered
  4. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-a042ce57d2ee498f8a5c6dbd5249b893
Source dataset
uspto-grants-1997_06
Patent number
US05641886

Reaction notes

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