tert-Butyl methyl ether → Ceramide NG

HRID 222837Notes

Reaction equation

HRID 222837 reaction equation
COC(C)(C)C.[C:7]([NH:26][C@H:27]([C@H:33]([OH:49])[CH2:34][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][CH3:48])[C:28](OCC)=[O:29])(=[O:25])[CH2:8][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][CH3:24].[BH4-].[Na+]>O>[C:7]([NH:26][C@H:27]([C@H:33]([OH:49])[CH2:34][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][CH3:48])[CH2:28][OH:29])(=[O:25])[CH2:8][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][CH3:24]

Participants

5

Reactant 3

HCID 15413tert-Butyl methyl etherHCID 4311764Sodium borohydrideHCID 86638488ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate

Product 1

HCID 5283573Ceramide NGYield 95.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

A t-butyl methyl ether suspension (2 mL) containing ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate (100 mg. 0.16 mmol) synthesized in the same method as Example 17 and sodium borohydride (20.3 mg, 0.54 mmol) was stirred at 23° C. for 48 hours. After water (5 mL) was added thereto, the reaction mixture was separated at 40° C. to separate the organic layer. It was confirmed by comparative analysis of the obtained organic layer with sample product using HPLC that the organic layer contained 86.6 mg of the title compound (yield: 93%). HPLC analysis was carried out to find that anti-form:syn-form was 93:7 and the optical purity of the anti-form was 100% ee.

Workup

  1. customthe reaction mixture was separated at 40° C.
  2. customto separate the organic layer

Sources & evidence

ORD record
ord-40e341d1f13d45c7bb4e2e69145116c9
Source dataset
uspto-grants-2012_06
Patent number
US08207370B2

Reaction notes

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