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Formic Acid → ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate

HRID 222834
ノート
印刷プレビュー

反応式

HRID 222834 の反応式
C(Cl)Cl.C(N(CC)CC)C.C(O)=O.[C:14]([NH:33][CH:34]([C:40](=[O:56])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[C:35]([O:37][CH2:38][CH3:39])=[O:36])(=[O:32])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>O>[C:14]([NH:33][C@H:34]([C@H:40]([OH:56])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[C:35]([O:37][CH2:38][CH3:39])=[O:36])(=[O:32])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 284Formic AcidHCID 6344Dichloromethane3 回HCID 8471TriethylamineHCID 24880587Ethyl 2-octadecanoylamino-3-oxooctadecanoate

生成物 1

HCID 86638488ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate収率 90%

試薬・触媒・溶媒 1

HCID 962
Water
溶媒

実験手順

A methylene chloride solution (0.5 ml) of triethylamine (131.6 mg, 1.30 mmol) and a methylene chloride solution (0.5 ml) of formic acid (64.5 mg, 1.37 mmol) were added to a methylene chloride solution (4.0 ml) of RuCl[(R,R)-TsDPEN](p-cymene) complex (18.9 mg, 0.03 mmol) and ethyl 2-octadecanoylamino-3-oxooctadecanoate (121.6 mg, 0.20 mmol) synthesized in the same method as Example 9. After the mixture was stirred for 16 hours at room temperature, water was added thereto and extraction with methylene chloride was carried out three times. After the organic layers were combined and dried with magnesium sulfate, the solvent was removed in reduced pressure. The obtained crude product was purified by silica gel chromatography (Kieselgel 60 manufactured by Merck, hexane:ethyl acetate=4:1) to obtain the title compound (109.6 mg, yield: 90%). The product was analyzed by HPLC to find that anti-form:syn-form was 91:9 and the optical purity of the anti-form was 95% ee.

後処理

  1. customsynthesized in the same method as Example 9
  2. extractionextraction with methylene chloride
  3. dry with materialdried with magnesium sulfate
  4. customthe solvent was removed in reduced pressure
  5. customThe obtained crude product
  6. customwas purified by silica gel chromatography (Kieselgel 60 manufactured by Merck, hexane:ethyl acetate=4:1)

出典と根拠

ORDレコード
ord-02651ce7279d4098a74f9e3f22316305
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08207370B2

反応ノート

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