p-Toluenesulfonic acid → 5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-2(S),7(S)-diisopropyl-8-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-octanoic acid [N-(1-carbamoyl-1-methyl-ethyl)]-amide

HRID 264949Notes

Reaction equation

HRID 264949 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:12]([O:16][C:17]([N:19]1[C@@H:23]([CH2:24][C@@H:25]([CH:41]([CH3:43])[CH3:42])[CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH2:36][CH2:37][CH2:38][O:39][CH3:40])[CH:28]=2)[C@H:22]([CH2:44][C@H:45]([C:49](=[O:57])[NH:50][C:51]([C:54](=[O:56])[NH2:55])([CH3:53])[CH3:52])[CH:46]([CH3:48])[CH3:47])[O:21]C1(C)C)=[O:18])([CH3:15])([CH3:14])[CH3:13]>CO>[C:54]([C:51]([NH:50][C:49](=[O:57])[C@H:45]([CH:46]([CH3:48])[CH3:47])[CH2:44][C@H:22]([OH:21])[C@@H:23]([NH:19][C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:18])[CH2:24][C@@H:25]([CH:41]([CH3:43])[CH3:42])[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH2:36][CH2:37][CH2:38][O:39][CH3:40])[CH:28]=1)([CH3:52])[CH3:53])(=[O:56])[NH2:55]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 228657843-Tert-butoxycarbonyl-5(S)-{2-[N-(1-carbamoyl-1-methyl-ethyl)-carbamoyl]-2(S)-isopropyl-ethyl}-4(S)-{2(S)-isopropyl-3-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-propyl}-2,2-dimethyl-1,3-oxazolidine

Product 1

HCID 236270705(S)-tert-butoxycarbonylamino-4(S)-hydroxy-2(S),7(S)-diisopropyl-8-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-octanoic acid [N-(1-carbamoyl-1-methyl-ethyl)]-amide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5 mg of p-toluenesulfonic acid (monohydrate) are added to 82 mg of 3-tert-butoxycarbonyl-5(S)-{2-[N-(1-carbamoyl-1-methyl-ethyl)-carbamoyl]-2(S)-isopropyl-ethyl}-4(S)-{2(S)-isopropyl-3-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-propyl}-2,2-dimethyl-1,3-oxazolidine in 5 ml of methanol at 0° C. The reaction solution is stirred for a further 18 hours at room temperature. After evaporation of the solvent, 20 ml of saturated sodium hydrogen carbonate solution are added to the residue and extraction is carried out repeatedly with ethyl acetate. The organic extracts are concentrated by evaporation and purified by means of FC (35 g of silica gel, dichloromethane/methanol=9:1). The title compound is obtained:Rf (dichloromethane/methanol=9:1)=0.47.

Workup

  1. customAfter evaporation of the solvent, 20 ml of saturated sodium hydrogen carbonate solution
  2. additionare added to the residue and extraction
  3. concentrationThe organic extracts are concentrated by evaporation
  4. custompurified by means of FC (35 g of silica gel, dichloromethane/methanol=9:1)

Sources & evidence

ORD record
ord-533551301c504a35a0d5b63f753915a4
Source dataset
uspto-grants-1997_07
Patent number
US05646143

Reaction notes

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