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Hexacosanoic Acid → HCID 117778469, 화합물

HRID 2201763
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HRID 2201763 반응식
C(Cl)(C(Cl)=O)=O.[C:7]([OH:34])(=O)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][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][CH2:31][CH3:32].[NH2:35][C@@H:36]([C@@H:49]([OH:66])[C@@H:50]([OH:65])[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH3:64])[CH2:37][O:38][C@@H:39]1[CH2:45][CH2:44][CH2:43][C@H:42]([OH:46])[C@H:41]([OH:47])[C@H:40]1[OH:48]>C1COCC1.CC([O-])=O.[Na+]>[OH:66][C@@H:49]([C@@H:50]([OH:65])[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH3:64])[C@H:36]([NH:35][C:7](=[O:34])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][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][CH2:31][CH3:32])[CH2:37][O:38][C@H:39]1[CH2:45][CH2:44][CH2:43][C@H:42]([OH:46])[C@H:41]([OH:47])[C@H:40]1[OH:48]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 10469Hexacosanoic AcidHCID 65578Oxalyl chlorideHCID 117778748HCID 117778748, 화합물

생성물 1

HCID 117778469HCID 117778469, 화합물

시약·촉매·용매 1

HCID 23696006HCID 23696006, 화합물용매

반응 조건

온도
70 °C

실험 절차

(COCl)2 (2 mL) was added to hexacosanoic acid (139 mg, 0.39 mmol) and heated at 70° C. for 2 h, after which time the solution was cooled to rt, and the (COCl)2 removed under a stream of dry argon. The residual volatiles were removed under reduced pressure. The resulting crude acyl chloride was dissolved in THF (0.5 mL) and added with vigorous stirring to a solution of amine 72 (81 mg, 0.18 mmol) in THF/NaOAc(aq) (8M) (1:1, 2 mL). Vigorous stirring was maintained for 2 h, after which time the reaction mixture was left to stand and the layers were separated. The aqueous layer was extracted with THF (3×2.0 mL) and the organic layers were combined and concentrated under reduced pressure. The crude product was purified by column chromatography (10% MeOH in CHCl3) to give amide 73 as a white solid.

후처리

  1. temperatureafter which time the solution was cooled to rt
  2. customthe (COCl)2 removed under a stream of dry argon
  3. customThe residual volatiles were removed under reduced pressure
  4. dissolutionThe resulting crude acyl chloride was dissolved in THF (0.5 mL)
  5. additionadded
  6. temperaturewas maintained for 2 h
  7. waitafter which time the reaction mixture was left
  8. customthe layers were separated
  9. extractionThe aqueous layer was extracted with THF (3×2.0 mL)
  10. concentrationconcentrated under reduced pressure
  11. customThe crude product was purified by column chromatography (10% MeOH in CHCl3)

출처 및 근거

ORD 기록
ord-56ba5e9e259c46459fc7c9470c682c8e
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09365496B2

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