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

HRID 222833Notes

Reaction equation

HRID 222833 reaction equation
C(N(CC)CC)C.C(O)=O.[CH:11]([NH:13][CH:14]([C:20](=[O:36])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:12]>C1COCC1>[CH:11]([NH:13][C@H:14]([C@H:20]([OH:36])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:12]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 86638485Ethyl 2-formylamino-3-oxooctadecanoate

Product 1

HCID 86638487ethyl (2R,3R)-2-formylamino-3-hydroxyoctadecanoateYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A dehydrated THF solution (0.5 ml) of triethylamine (131.7 mg, 1.30 mmol) and a dehydrated THF solution (0.5 ml) of formic acid (64.2 mg, 1.37 mmol) were added to a dehydrated THF solution (4.0 ml) of RuCl[(R,R)-TsDPEN](p-cymene) complex (19.6 mg, 0.03 mmol) and ethyl 2-formylamino-3-oxooctadecanoate (73.5 mg, 0.20 mmol) synthesized in the same method as Example 8. After the mixture was stirred for 3 days at room temperature, the reaction solvent was removed in reduced pressure. Water was added thereto and extraction with ethyl acetate was carried out three times. The organic layers were combined and dried with magnesium sulfate. After 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=1:2) to obtain the title compound (64.6 mg, yield: 87%). The product was analyzed by HPLC to find that anti-form:syn-form was 95:5 and the optical purity of the anti-form was 96% ee.

Workup

  1. customsynthesized in the same method as Example 8
  2. customthe reaction solvent was removed in reduced pressure
  3. additionWater was added
  4. extractionextraction with ethyl acetate
  5. dry with materialdried with magnesium sulfate
  6. customAfter the solvent was removed in reduced pressure
  7. customthe obtained crude product
  8. customwas purified by silica gel chromatography (Kieselgel 60 manufactured by Merck, hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-d5ec49a4c59446458738ce53a923cd08
Source dataset
uspto-grants-2012_06
Patent number
US08207370B2

Reaction notes

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