Hydrochloric Acid → HCID 44177830, compound

HRID 1254178Notes

Reaction equation

HRID 1254178 reaction equation
[Cl:1][C@H:2]1[C@H:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15]CCC)=[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][CH2:8][CH2:9][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 57814831HCID 57814831, compound

Product 1

HCID 44177830HCID 44177830, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 137 mg (0.31 mmol) of ester 16 in 2 mL of THF was hydrolyzed with 800 uL (0.40 mmol) of aqueous lithium hydroxide (0.5M) and 1 mL of methanol at 25° C. for 6 h. The mixture was acidified to pH 5-6 by addition of 400 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 8% methanol:92% EtOAc, then 10% methanol:90% ethyl acetate. Isolated from appropriate fractions was 110 mg of free acid 17 as an oil (88% yield); 1H NMR (acetone-d6): 1.13 (d, J=6.3 Hz, 3H), 1.16-1.68 (m, 13H), 1.86 (m, 1H), 2.0-2.24 (m, 3H), 2.29 (t, J=7.5 Hz, 2H), 3.73 (m, 1H), 4.09 (m, 3H), 5.56 (m, 2H). LC-MS 373.3 [M++1-H2O].

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 8% methanol
  4. customIsolated from appropriate fractions

Sources & evidence

ORD record
ord-42a8ccb6e413452990b7d4172bc5dc33
Source dataset
uspto-grants-2013_06
Patent number
US08455547B2

Reaction notes

Loading…