p-Toluenesulfonic acid monohydrate → HCID 22882390, compound

HRID 863289Notes

Reaction equation

HRID 863289 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C:14]2([CH2:17][CH2:18][O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:16][CH2:15]2)[CH2:11][O:10]C1(C)C)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[C:1]([O:5][C:6]([NH:8][C@@H:12]([CH2:13][C:14]1([CH2:17][CH2:18][O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:15][CH2:16]1)[CH2:11][OH:10])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 22882478HCID 22882478, compound

Product 1

HCID 22882390HCID 22882390, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 23.9 g of 3-tert-butoxycarbonyl-2,2-dimethyl-4(S)-[1-(2-benzyloxyethyl)cyclopropylmethyl]1,3-oxazolidine, 0.67 g of p-toluenesulfonic acid hydrate and 100 ml of methanol is stirred at room temperature for 5 h. After the reaction mixture has been concentrated, diethyl ether is added. The organic phase is washed with saturated sodium bicarbonate solution and saturated sodium chloride solution and added over sodium sulfate. The crude product is purified by means of FC over 900 g of silica gel (mobile phase gradient from E to A): Rf (C)=0.26; anal. calc. for C20H31NO4 : C68.74%, H8.94%, N4.01%; found C68.44%, H8.93%, N4.09%.

Workup

  1. concentrationAfter the reaction mixture has been concentrated
  2. additiondiethyl ether is added
  3. washThe organic phase is washed with saturated sodium bicarbonate solution and saturated sodium chloride solution
  4. additionadded over sodium sulfate
  5. customThe crude product is purified by means of FC over 900 g of silica gel (mobile phase gradient from E to A): Rf (C)=0.26

Sources & evidence

ORD record
ord-82b3aad87fc14af8814028deca4d7494
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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