p-Toluenesulfonic acid → HCID 53714532, compound

HRID 375728Notes

Reaction equation

[Si:1]([O:8][C:9]1[C:10]([CH2:32][S:33][CH2:34][C@H:35]([NH:40][C:41](=[O:64])[CH2:42][CH2:43][O:44]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:36]([O:38][CH3:39])=[O:37])=[C:11]([C:20]([CH3:31])=[C:21]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH:22]=1)[C:12]([O:14][CH2:15][C:16]([Cl:19])([Cl:18])[Cl:17])=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[Si:1]([O:8][C:9]1[C:10]([CH2:32][S:33][CH2:34][C@H:35]([NH:40][C:41](=[O:64])[CH2:42][CH2:43][OH:44])[C:36]([O:38][CH3:39])=[O:37])=[C:11]([C:20]([CH3:31])=[C:21]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH:22]=1)[C:12]([O:14][CH2:15][C:16]([Cl:18])([Cl:19])[Cl:17])=[O:13])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 6.85 g of 2,2,2-trichloroethyl (R)-3,5-bis (tert-butyldimethylsilyloxy)-6-methyl-2-[[[2-(3-trityloxypropionylamino)-2-(methoxycarbonyl)ethyl] thio]methyl]benzoate and 0.11 g of p-toluenesulfonic acid in 115 ml of methanol was stirred at 60° C. for 30 minutes. The mixture was cooled and the solvent was evaporated in vacuo. Chromatography of the residue on silica gel using ethyl acetate/methylene chloride/hexane (1:1:1, v/v/v) as eluent afforded 3.97 g of 2,2,2-trichloroethyl (R)-3,5-bis(tert-butyldimethylsilyloxy)2-[[[2-(3-hydroxypropionylamino)-2-(methoxycarbonyl)ethyl]thio]methyl]-6-methyl-benzoate as white-off solid.

Workup

temperatureThe mixture was cooled
customthe solvent was evaporated in vacuo

Sources & evidence

ORD record: ord-0b6662e49a2c4a9086c0bd41bbe18086
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05486466

Reaction notes

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