Potassium Carbonate → 3-[(3R)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]propyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate

HRID 1747021Notes

Reaction equation

HRID 1747021 reaction equation
[C:1]([OH:22])(=[O:21])[CH2:2][CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7]/[CH:8]=[CH:9]\[CH2:10]/[CH:11]=[CH:12]\[CH2:13]/[CH:14]=[CH:15]\[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH3:20].C([O-])([O-])=O.[K+].[K+].Cl[CH2:30][CH2:31][CH2:32][N:33]1[CH2:38][C@H:37]([OH:39])[C@@H:36]([OH:40])[C@H:35]([OH:41])[C@H:34]1[CH2:42][OH:43]>CN(C=O)C>[C:1]([O:22][CH2:30][CH2:31][CH2:32][N:33]1[CH2:38][CH:37]([OH:39])[CH:36]([OH:40])[C@H:35]([OH:41])[CH:34]1[CH2:42][OH:43])(=[O:21])[CH2:2][CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7]/[CH:8]=[CH:9]\[CH2:10]/[CH:11]=[CH:12]\[CH2:13]/[CH:14]=[CH:15]\[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 446284IcosapentHCID 118407747(2R,3R,4R,5S)-1-(3-chloropropyl)-2-(hydroxymethyl)piperidine-3,4,5-triol

Product 1

HCID 1317335533-[(3R)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]propyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

To a stirred solution of (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid 6 (6.94 g, 22.95 mmol) in DMF (25 mL) was added K2CO3 (12.69 g, 91.78 mmol) at room temperature and the mixture was stirred for 30 min. Then a solution of hydrochloride salt of (2R,3R,4R,5S)-1-(3-chloropropyl)-2-(hydroxymethyl)piperidine-3,4,5-triol 5 (5.5 g, 22.95 mmol) in DMF (25 mL) was added to the reaction mixture and the mixture was heated at 60° C. for 36 h. The reaction mixture was then filtered through a celite pad, washed with DCM (100 mL). The filtrate was concentrate under reduced pressure to get crude which was purified by column chromatography using 100-200 mesh silica gel and eluting with 6% methanol in DCM to afford 3-[(3R)-3,4,5-trihydroxy-2-(hydroxymethyl)piperidin-1-yl]propyl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate, compound 7 (4.5 g, 39%) as brown oil.

Workup

  1. filtrationThe reaction mixture was then filtered through a celite pad
  2. washwashed with DCM (100 mL)
  3. concentrationThe filtrate was concentrate under reduced pressure
  4. customto get crude which
  5. customwas purified by column chromatography
  6. washeluting with 6% methanol in DCM

Sources & evidence

ORD record
ord-9aa99806ad2f4d7491bb9d21d75236ee
Source dataset
uspto-grants-2015_10
Patent number
US09150557B1

Reaction notes

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