Tetrahydrofuran → Ceramide NG

HRID 222839Notes

Reaction equation

HRID 222839 reaction equation
C1COCC1.[BH4-].[Na+].[C:8]([NH:27][C@H:28]([C@H:34]([OH:50])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[C:29](OCC)=[O:30])(=[O:26])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].C(OCC)(=O)C>O>[C:8]([NH:27][C@H:28]([C@H:34]([OH:50])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH2:29][OH:30])(=[O:26])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 86638488ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate

Product 1

HCID 5283573Ceramide NGYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A THF suspension (2 mL) containing sodium borohydride (39.2 mg, 0.96 mmol) was heated to 60° C., and ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate (300.0 mg, 0.49 mmol) synthesized in the same manner as Example 17 was added for 2.5 hours. After completion of the dropwise addition, the mixture was further stirred at 60° C. for 24 hours. After ethyl acetate and water were added thereto, the reaction mixture was stirred at 60° C. for 1 hour. After the organic layer was separated, the obtained organic layer was washed with saturated brine and dried with magnesium sulfate. The solvent was removed in reduced pressure. It was confirmed that 219.4 mg of the title compound was contained (yield: 78%). HPLC analysis was carried out to find that anti-form:syn-form was 81:19 and the optical purity of the anti-form was 99% ee.

Workup

  1. additionwas added for 2.5 hours
  2. additionAfter completion of the dropwise addition
  3. stirringthe reaction mixture was stirred at 60° C. for 1 hour
  4. customAfter the organic layer was separated
  5. washthe obtained organic layer was washed with saturated brine
  6. dry with materialdried with magnesium sulfate
  7. customThe solvent was removed in reduced pressure

Sources & evidence

ORD record
ord-b0a085b9cb4c4fdaa5253fe6e0d41899
Source dataset
uspto-grants-2012_06
Patent number
US08207370B2

Reaction notes

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