HCID 58646747, compound → HCID 69203352, compound

HRID 902001Notes

Reaction equation

HRID 902001 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][C@H:13]1[OH:22])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[CH2:1]([O:8][C:9]([NH:11][CH:12]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][C:13]1=[O:22])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 58646747HCID 58646747, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 69203352HCID 69203352, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of trans 3-benzyloxycarbonylamino-2-hydroxy-1,2,3,4-tetrahydronaphthalene (850 mg) in dichloromethane (29 mL) stirring under nitrogen at room temperature was added pyridinium chlorochromate (740 mg). After 3 h, the reaction mixture was evaporated under vacuum onto silica gel and then purified by silica gel chromatography eluting with a step-wise gradient of 30-75% ethyl acetate in hexane to obtain the title compound (300 mg) as a white solid and starting material (350 mg).

Workup

  1. customthe reaction mixture was evaporated under vacuum onto silica gel
  2. custompurified by silica gel chromatography
  3. washeluting with a step-wise gradient of 30-75% ethyl acetate in hexane

Sources & evidence

ORD record
ord-398de12d78c04bb78ca398d331248f41
Source dataset
uspto-grants-2008_04
Patent number
US07365061B2

Reaction notes

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