Acetic Acid → HCID 59463747, compound

HRID 1010624Notes

Reaction equation

HRID 1010624 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:16]=[C:17]([C:25]([OH:27])=[O:26])[C:18]3[C:23]([CH:24]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:28][Si](C=[N+]=[N-])(C)C.C(O)(=O)C>CO.CCOCC>[OH:14][C:11]1([C:15]2[CH:16]=[C:17]([C:25]([O:27][CH3:28])=[O:26])[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:24]=2)[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 167693TrimethylsilyldiazomethaneHCID 67297086HCID 67297086, compound

Product 1

HCID 59463747HCID 59463747, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 1.3 g (3.5 mmol) of the above 3-[1-(tert-butoxycarbonyl)-4-hydroxypiperidin-4-yl]-1-naphthoic acid in 10 mL of methanol and 10 mL of ether was added 2.0 mL (4.0 mmol) of a 2.0 M solution of (trimethylsilyl)diazomethane in ether. Glacial acetic acid was the added dropwise until gas evolution ceased and then the reaction was concentrated in vacuo to yield the crude title compound as a yellow oil. LC/MS 408.1 (M+23).

Workup

  1. additionadded dropwise until gas evolution
  2. concentrationthe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-94ccb64315b441489ac19f3f4199a864
Source dataset
uspto-grants-2011_07
Patent number
US07977339B2

Reaction notes

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