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

HRID 222835Notes

Reaction equation

HRID 222835 reaction equation
C(N(CC)CC)C.C(O)=O.ClC1C=CC=CC=1.[C:18]([NH:37][CH:38]([C:44](=[O:60])[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])[C:39]([O:41][CH2:42][CH3:43])=[O:40])(=[O:36])[CH2:19][CH2:20][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]>O>[C:18]([NH:37][C@H:38]([C@H:44]([OH:60])[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])[C:39]([O:41][CH2:42][CH3:43])=[O:40])(=[O:36])[CH2:19][CH2:20][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]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 7964ChlorobenzeneHCID 8471TriethylamineHCID 24880587Ethyl 2-octadecanoylamino-3-oxooctadecanoate

Product 1

HCID 86638488ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoateYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

Triethylamine (830 mg, 8.20 mmol) and formic acid (227 mg, 4.93 mmol) were added to a chlorobenzene solution (15.0 ml) of RuCl[(R,R)-TsDPEN](p-cymene) complex (11.0 mg, 0.03 mmol) and ethyl 2-octadecanoylamino-3-oxooctadecanoate (1.00 g, 1.64 mmol) synthesized in the same method as Example 10. After the reaction mixture was stirred for 3 days at 40° C., water (10 mL) was added thereto and separation operation was carried out at 40° C. to obtain the organic layer. After the organic layer was concentrated until the total amount became 3.11 g, 10 mL of AcOEt was added thereto and recrystallization was carried out to obtain 0.73 g of the title compound (yield: 74%). Anti-form:syn-form was 100:0 and the optical purity of the anti-form was 100% ee.

Workup

  1. customsynthesized in the same method as Example 10
  2. customseparation operation
  3. customwas carried out at 40° C.
  4. customto obtain the organic layer
  5. concentrationAfter the organic layer was concentrated until the total amount
  6. additionwas added
  7. customrecrystallization

Sources & evidence

ORD record
ord-1258655ab6764efda0d1694134f75ab5
Source dataset
uspto-grants-2012_06
Patent number
US08207370B2

Reaction notes

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