Acetic Acid → HCID 89668329, compound

HRID 1482243Notes

Reaction equation

HRID 1482243 reaction equation
C(OC([NH:8][C@H:9]([C:28](=[O:35])[N:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[CH2:10][C:11]1[CH:12]=[C:13]([C:17](=[CH2:27])[CH2:18][CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])[CH:14]=[CH:15][CH:16]=1)=O)(C)(C)C.C(O)(=O)C.[CH:40]1[C:52]2[CH:51]([CH2:53][O:54][C:55]([O:57]N3C(=O)CCC3=O)=O)[C:50]3[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=3)[C:44]=2[CH:43]=[CH:42][CH:41]=1>O.O1CCOCC1>[CH:45]1[C:50]2[CH:51]([CH2:53][O:54][C:55]([NH:8][C@H:9]([C:28](=[O:35])[N:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)[CH2:10][C:11]3[CH:12]=[C:13]([C:17](=[CH2:27])[CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH:14]=[CH:15][CH:16]=3)=[O:57])[C:52]3[C:44](=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:49]=2[CH:48]=[CH:47][CH:46]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 89668514HCID 89668514, compound

Product 1

HCID 89668329HCID 89668329, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl (S)-4-(3-(2-((tert-butoxycarbonyl)amino)-3-oxo-3-(piperidin-1-yl)propyl)phenyl)pent-4-enoate (Compound SP420) (0.50 g, 1.03 mmol) was suspended in acetic acid (7.0 ml, 122.28 mmol) and water (7.0 ml), and the suspension was stirred with heating at reflux for 8 hours. The same reaction was additionally carried out four times. The reaction solutions were combined and concentrated under reduced pressure, and the resulting residue was suspended in a 10% aqueous sodium carbonate solution (38 ml). A solution of N-(9-fluorenylmethoxycarbonyloxy)-succinimide (1.65 g, 4.89 mmol) in 1,4-dioxane (19.0 ml) was added and the mixture was stirred at room temperature for 1 hour. The reaction solution was washed with diethyl ether, made acidic by adding acetic acid and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure, and the resulting residue was purified by column chromatography (hexane:ethyl acetate=100:0-50:50) to afford the title compound SP421 (0.78 g, 27.5%).

Workup

  1. temperaturewith heating
  2. temperatureat reflux for 8 hours
  3. customThe same reaction
  4. concentrationconcentrated under reduced pressure
  5. washThe reaction solution was washed with diethyl ether
  6. additionby adding acetic acid
  7. extractionextracted with ethyl acetate
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customthe resulting residue was purified by column chromatography (hexane:ethyl acetate=100:0-50:50)

Sources & evidence

ORD record
ord-4f2073ecf6624cb89a6df93767fb60a2
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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