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

HRID 222834Notes

Reaction equation

HRID 222834 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-02651ce7279d4098a74f9e3f22316305
Source dataset
uspto-grants-2012_06
Patent number
US08207370B2

Reaction notes

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