Hydrochloric Acid → Ceramide NG

HRID 222840노트

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HRID 222840 반응식
[C:1]([NH:20][C@H:21]([C@H:27]([OH:43])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[C:22](OCC)=[O:23])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[BH4-].[Na+].[Cl-].[Al+3].[Cl-].[Cl-].Cl>O.C1COCC1>[C:1]([NH:20][C@H:21]([C@H:27]([OH:43])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:22][OH:23])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 6451240Aluminum(III) ChlorideHCID 86638488ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate

생성물 1

HCID 5283573Ceramide NG수율 84.5%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

Ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate (1.50 g, 2.46 mmol) synthesized in the same manner as Example 17 was added to a THF suspension (15 mL) containing sodium borohydride (271.9 mg, 7.38 mmol) at room temperature for 0.5 hours. After completion of the dropwise addition, aluminum chloride (984.0 mg, 7.38 mmol) was added for 1 hour. After water was added to the reaction mixture, concentrated hydrochloric acid was added thereto to adjust pH of the mixture to be 1.5. The resulting reaction mixture was further stirred at 50° C. for 1 hour, and the organic layer was separated. It was confirmed by comparative analysis of the organic layer with sample product using HPLC that the organic layer contained 1.18 g of the title compound (yield: 84%). It was also found that anti-form:syn-form was 98:2 and the optical purity of the anti-form was 97% ee.

후처리

  1. additionwas added for 1 hour
  2. additionwas added
  3. customThe resulting reaction mixture
  4. customthe organic layer was separated

출처 및 근거

ORD 기록
ord-20623c3c66cf484a95c339287bc09b86
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207370B2

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