p-Toluenesulfonic acid → 2-{1 (S)-tert-butoxycarbonylamino-3(S)-isopropyl-4-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-butyl}-4(R)-methyl-tetrahydrofuran-5-one

HRID 744829Notes

Reaction equation

HRID 744829 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N[C:17](=[O:52])[C@H:18]([CH3:51])[CH2:19][C@H:20]([OH:50])[C@@H:21]([NH:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:22][C@@H:23]([CH:39]([CH3:41])[CH3:40])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH2:34][CH2:35][CH2:36][O:37][CH3:38])[CH:26]=1)CCC>C(Cl)(Cl)Cl>[C:46]([O:45][C:43]([NH:42][C@H:21]([CH:20]1[CH2:19][C@@H:18]([CH3:51])[C:17](=[O:52])[O:50]1)[CH2:22][C@@H:23]([CH:39]([CH3:40])[CH3:41])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH2:34][CH2:35][CH2:36][O:37][CH3:38])[CH:26]=1)=[O:44])([CH3:49])([CH3:48])[CH3:47]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 236251841,1-Dimethylethyl N-((1S,2S,4R)-5-(butylamino)-2-hydroxy-1-((2S)-2-((4-methoxy-3-(3-methoxypropoxy)phenyl)methyl)-3-methylbutyl)-4-methyl-5-oxopentyl)carbamate

Product 1

HCID 228657322-{1 (S)-tert-butoxycarbonylamino-3(S)-isopropyl-4-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-butyl}-4(R)-methyl-tetrahydrofuran-5-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2.02 g of p-toluenesulfonic acid (monohydrate) are added to 5.6 g of 5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-7(S)-isopropyl-2(R)-methyl-8-[4-methoxy-3-(3-methoxy-propyloxy)-phenyl]-octanoic acid (N-butyl)-amide (Example 32) in 240 ml of chloroform at room temperature and the mixture is stirred at room temperature for a further 18 hours. The reaction mixture is concentrated by evaporation and the residue is partitioned between diethyl ether and 0.1N hydrochloric acid. The organic phases are concentrated by evaporation and the title compound is obtained from the residue after FC (160 g of silica gel, eluant: ethyl acetate/hexane 1:1): Rf (ethyl acetate/hexane=2:1)=0.47; m.p. 86°-87° C.

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. customthe residue is partitioned between diethyl ether and 0.1N hydrochloric acid
  3. concentrationThe organic phases are concentrated by evaporation

Sources & evidence

ORD record
ord-7279caf1803e45b5911fad61f0e67347
Source dataset
uspto-grants-1996_09
Patent number
US05559111

Reaction notes

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