p-Toluenesulfonic acid monohydrate → HCID 91472268, compound

HRID 499697Notes

Reaction equation

HRID 499697 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C:14]([CH3:34])([CH3:33])[CH2:15][C:16]([N:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:21][CH:20]([NH:28][C:29]([O:31][CH3:32])=[O:30])[CH2:19]2)=[O:17])[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>C(Cl)Cl>[CH3:32][O:31][C:29](=[O:30])[NH:28][CH:20]1[CH2:21][C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:18]([C:16](=[O:17])[CH2:15][C:14]([CH3:34])([CH3:33])[CH2:13][C@H:12]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:11][OH:10])[CH2:19]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrate2×HCID 131728264HCID 131728264, compound

Product 1

HCID 91472268HCID 91472268, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3.1 g of 4(S)-[4-(3(R,S)-methoxycarbonylamino-3,4-dihydro-2H-quinolin-1-yl)-2,2-dimethyl-4-oxo-butyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester and 104 mg of p-toluenesulfonic acid monohydrate in 49 ml of methylene chloride under argon is stirred at room temperature for 3.5 hours. More p-toluenesulfonic acid monohydrate (200 mg) is added and the mixture is stirred at room temperature for 1.5 hours The solution is concentrated. The title compound is obtained as a white solid from the residue by means of flash chromatography (SiO2 60 F). Rf=0.14 (3:1 EtOAc-heptane); Rt=3.91 (gradient I).

Workup

  1. concentrationis concentrated

Sources & evidence

ORD record
ord-85bc492bd7df4943b58ad9a97c31265e
Source dataset
uspto-grants-2010_08
Patent number
US07767690B2

Reaction notes

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