Diazomethane → HCID 70377919, compound

HRID 845728Notes

Reaction equation

HRID 845728 reaction equation
[C:1]([C:8]([NH2:32])([CH2:12][CH2:13][CH2:14][C:15]1([CH2:21][C:22]([O:24]CC2C=CC=CC=2)=[O:23])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[C:9]([OH:11])=[O:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[N+](=[CH2:35])=[N-]>C(Cl)Cl>[C:1]([C:8]([NH2:32])([CH2:12][CH2:13][CH2:14][C:15]1([CH2:21][C:22]([OH:24])=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1)[C:9]([O:11][CH3:35])=[O:10])([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 131715644HCID 131715644, compound

Product 1

HCID 70377919HCID 70377919, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The Boc-benzyl ester (J) (4 mmol) is dissolved in methylene chloride and treated with excess ethereal diazomethane at room temperature. The residual diazomethane is quenched with acetic acid and the solution is evaporated at reduced pressure. The crude diester is dissolved in methanol and hydrogenated over 10% palladium-on-carbon to give, after flash chromatography (silica gel), the titled compound.

Workup

  1. customThe residual diazomethane is quenched with acetic acid
  2. customthe solution is evaporated at reduced pressure
  3. dissolutionThe crude diester is dissolved in methanol
  4. customto give

Sources & evidence

ORD record
ord-07c7d16b8b3945cebd09dd249b6fcb60
Source dataset
uspto-grants-1988_07
Patent number
US04760052

Reaction notes

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