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

HRID 222835
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HRID 222835 반응식
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]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962
Water
용매

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온도
40 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1258655ab6764efda0d1694134f75ab5
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08207370B2

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