Hydrochloric Acid → HCID 44193926, compound

HRID 1254172Notes

Reaction equation

HRID 1254172 reaction equation
[Cl:1][C@H:2]1[C@H:6]([CH2:7]/[CH:8]=[CH:9]\[CH2:10][CH2:11][CH2:12][C:13]([O:15]CC=C)=[O:14])[C@@H:5](/[CH:19]=[CH:20]/[C@@H:21]([OH:28])[CH2:22][CH2:23][CH2:24][C@H:25]([OH:27])[CH3:26])[C@H:4]([OH:29])[CH2:3]1.[OH-].[Li+].CO.Cl>C1COCC1>[Cl:1][C@H:2]1[C@H:6]([CH2:7]/[CH:8]=[CH:9]\[CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[C@@H:5](/[CH:19]=[CH:20]/[C@@H:21]([OH:28])[CH2:22][CH2:23][CH2:24][C@H:25]([OH:27])[CH3:26])[C@H:4]([OH:29])[CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 57814828HCID 57814828, compound

Product 1

HCID 44193926HCID 44193926, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 77 mg (0.18 mmol) of ester 9 in 1.4 mL of THF was hydrolyzed with 400 uL (0.18 mmol) of aqueous lithium hydroxide (0.5M) and 0.4 mL of methanol at 25° C. for 5 h. The mixture was acidified by addition of 200 uL of 1.0M hydrochloric acid and the residual water was removed in vacuo. The residual products were purified by FCC on 10 g of silica gel eluted with 100% EtOAc, 5% methanol:95% EtOAc, then 10% methanol:90% ethyl acetate. Isolated from appropriate fractions was 49 mg of free acid 10 as an oil (70% yield); 1H NMR (acetone-d6): 1.11 (d, J=6.3 Hz, 3H), 1.45 (m, 6H), 1.67 (m, 2H), 1.91 (m, 1H), 2.09-2.37 (m, 8H), 2.86 (br s, 4H), 3.71 (m, 1H), 4.12 (m, 3H), 5.54 (m, 4H).

Workup

  1. customthe residual water was removed in vacuo
  2. customThe residual products were purified by FCC on 10 g of silica gel
  3. washeluted with 100% EtOAc, 5% methanol
  4. customIsolated from appropriate fractions

Sources & evidence

ORD record
ord-6e9b216e50724115b0f4087a26d1fa6f
Source dataset
uspto-grants-2013_06
Patent number
US08455547B2

Reaction notes

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