Hydrochloric Acid → Ceramide NG

HRID 222840ノート

反応式

HRID 222840 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 5283573Ceramide NG収率 84.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-20623c3c66cf484a95c339287bc09b86
出典データセット
uspto-grants-2012_06
特許番号
US08207370B2

反応ノート

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