tert-Butyl methyl ether → Ceramide NG

HRID 222837노트

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HRID 222837 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

HCID 5283573Ceramide NG수율 95.3%

시약·촉매·용매 1

HCID 962Water용매

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온도
23 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-40e341d1f13d45c7bb4e2e69145116c9
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207370B2

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