Hydrochloric Acid → HCID 57440695, compound

HRID 2102352Notes

Reaction equation

HRID 2102352 reaction equation
C[O:2][C:3](=[O:27])[C:4]1[CH:9]=[C:8]([CH:10]2[O:15][CH2:14][CH2:13][N:12]([CH2:16][CH2:17][CH3:18])[CH2:11]2)[CH:7]=[CH:6][C:5]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[OH-].[Na+].Cl>CO>[CH2:20]([O:19][C:5]1[CH:6]=[CH:7][C:8]([CH:10]2[O:15][CH2:14][CH2:13][N:12]([CH2:16][CH2:17][CH3:18])[CH2:11]2)=[CH:9][C:4]=1[C:3]([OH:27])=[O:2])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57440694HCID 57440694, compound

Product 1

HCID 57440695HCID 57440695, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the methyl ester from example 32 (105 mg, 0.28 mmol) in methanol (5 ml) was added 10% sodium hydroxide (aq) (15 ml) and the milky white suspension was refluxed for 2 hours. The now colourless reaction mixture was cooled then neutralised by addition of 2M HCl (aq) (few drops). The reaction mixture was then concentrated in vacuo to give the title compound as an off-white solid (99 mg, 0.28 mmol, 100%). LRMS: m/z 355 (M-H+). This material was taken on crude to example 34.

Workup

  1. temperaturethe milky white suspension was refluxed for 2 hours
  2. temperatureThe now colourless reaction mixture was cooled
  3. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-7482d4c32eb34b23a9e1efdabf62b216
Source dataset
uspto-grants-2009_08
Patent number
US07576081B2

Reaction notes

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