Hydrochloric Acid → HCID 18428670, compound

HRID 1279634Notes

Reaction equation

HRID 1279634 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[O:15][C:16]1[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][CH:17]=1)[C:8]([O:10]C)=[O:9])[CH3:3].[OH-].[Li+].Cl>C1COCC1>[CH3:3][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[O:15][C:16]1[CH:17]=[CH:18][C:19]([S:22][CH3:23])=[CH:20][CH:21]=1)[C:8]([OH:10])=[O:9])[CH3:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 18428707HCID 18428707, compound

Product 1

HCID 18428670HCID 18428670, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The ester from example 152 (5.22 g, 15.8 mmol) was dissolved in THF (60 mL), treated with aqueous lithium hydroxide (1 M, 63.1 mmol) and heated at reflux overnight. The reaction was neutralised with hydrochloric acid (2 M) and extracted with DCM. The organic extracts were dried (MgSO4) and evaporated to a white foam of the title carboxylic acid (4.80 g, 95%); δH (CD3OD, 400 MHz) 2.48 (3 H, s), 2.56 (6 H, s), 3.94 (2 H, s), 6.80 (1 H, d), 7.00 (2 H, d), 7.33 (2 H, d), 7.94 (1 H, d), 8.09 (1 H, s); MS m/z (ES+) 318 (MH+).

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. extractionextracted with DCM
  4. dry with materialThe organic extracts were dried (MgSO4)
  5. customevaporated to a white foam of the title carboxylic acid (4.80 g, 95%)

Sources & evidence

ORD record
ord-5b79db30f5304011ae9d281eaf4a6f54
Source dataset
uspto-grants-2002_09
Patent number
US06448293B1

Reaction notes

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