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

HRID 222834
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HRID 222834 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 284Formic AcidHCID 6344Dichloromethane3회HCID 8471TriethylamineHCID 24880587Ethyl 2-octadecanoylamino-3-oxooctadecanoate

생성물 1

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

시약·촉매·용매 1

HCID 962
Water
용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-02651ce7279d4098a74f9e3f22316305
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08207370B2

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