p-Tolyl chloroformate → HCID 68860532, compound

HRID 898885Notes

Reaction equation

HRID 898885 reaction equation
[C:1]([O:5][C:6](=[O:25])[C:7]([S:10][C:11]1[C:20]([Cl:21])=[CH:19][C:18]2[CH2:17][CH:16]([NH:22][CH2:23][CH3:24])[CH2:15][CH2:14][C:13]=2[CH:12]=1)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].Cl[C:27]([O:29][C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=1)=[O:28]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:25])[C:7]([S:10][C:11]1[C:20]([Cl:21])=[CH:19][C:18]2[CH2:17][CH:16]([N:22]([CH2:23][CH3:24])[C:27]([O:29][C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=3)=[O:28])[CH2:15][CH2:14][C:13]=2[CH:12]=1)([CH3:9])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 70304p-Tolyl chloroformateHCID 68862413HCID 68862413, compound

Product 1

HCID 68860532HCID 68860532, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-(3-chloro-6-ethylamino-5,6,7,8-tetrahydro-naphthalen-2-ylsulfanyl)-2-methyl-propionic acid tert-butyl ester and borane complex (80 mg; 201 μmol), dissolved in CH2Cl2 (2 mL), at 0° C. is added p-tolyl chloroformate (35 μL; 241 μmol). The reaction was slowly warmed to RT and allowed to stir at RT for 6 days. The solvent was removed under reduced pressure and the crude residue was purified by flash chromatography (SiO2) eluting with a hexanes-EtOAc gradient to afford 30 mg (29%) of 2-[3-chloro-6-(ethyl-p-tolyloxycarbonyl-amino)-5,6,7,8-tetrahydro-naphthalen-2-ylsulfanyl]-2-methyl-propionic acid tert-butyl ester as a clear oil.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude residue was purified by flash chromatography (SiO2)
  3. washeluting with a hexanes-EtOAc gradient

Sources & evidence

ORD record
ord-b2fdec74c2ce4092bf10769e1d793c81
Source dataset
uspto-grants-2008_04
Patent number
US07351857B2

Reaction notes

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