Formic Acid → HCID 86638486, compound

HRID 222830Notes

Reaction equation

HRID 222830 reaction equation
C(N(CC)CC)C.C(O)=O.[C:11]([NH:14][CH:15]([C:21](=[O:37])[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][CH2:35][CH3:36])[C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:13])[CH3:12]>C1COCC1>[C:11]([NH:14][C@H:15]([C@H:21]([OH:37])[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][CH2:35][CH3:36])[C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 86638484Ethyl 2-acetylamino-3-oxooctadecanoate

Product 1

HCID 86638486HCID 86638486, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A dehydrated THF solution (0.5 ml) of triethylamine (131.9 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-acetylamino-3-oxooctadecanoate (7.70 g, 0.20 mmol) synthesized in the same method as Example 1. After the mixture was stirred for 3 days at room temperature, the reaction solvent was removed in reduced pressure. Water was added thereto, and the mixture was extracted with ethyl acetate 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, solely ethyl acetate) to obtain the title compound (71.3 mg, yield: 94%). The product was analyzed by HPLC to find that anti-form:syn-form was 93:7 and the optical purity of the anti-form was 98% ee.

Workup

  1. customsynthesized in the same method as Example 1
  2. customthe reaction solvent was removed in reduced pressure
  3. additionWater was added
  4. extractionthe mixture was extracted with ethyl acetate three times
  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

Sources & evidence

ORD record
ord-3c1a68ad8f574226b8e748e0c3543c62
Source dataset
uspto-grants-2012_06
Patent number
US08207370B2

Reaction notes

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