Hexacosanoic acid → HCID 117778469, compound

HRID 2201763Notes

Reaction equation

HRID 2201763 reaction equation
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]

Participants

5

Reactant 3

HCID 10469Hexacosanoic acidHCID 65578Oxalyl chlorideHCID 117778748HCID 117778748, compound

Product 1

HCID 117778469HCID 117778469, compound

Reagents, catalysts & solvents 1

HCID 23696006HCID 23696006, compoundSolvent

Conditions

Temperature
70 °C

Procedure

(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.

Workup

  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)

Sources & evidence

ORD record
ord-56ba5e9e259c46459fc7c9470c682c8e
Source dataset
uspto-grants-2016_06
Patent number
US09365496B2

Reaction notes

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