Acetic Anhydride → HCID 59620355, compound

HRID 2070179Notes

Reaction equation

HRID 2070179 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]([CH2:12][C:13]1[CH:17]=[CH:16][S:15][CH:14]=1)[C:9](=[O:18])[CH:8]([NH:19][C:20](=[O:40])[C@H:21]([NH:26][C:27](=[O:39])[C:28]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:30])[CH3:29])[CH2:22][CH:23]([CH3:25])[CH3:24])[CH2:7]2.[C:41]1(=O)[O:46][C:44](=[O:45])[CH2:43][CH2:42]1.C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>O.C1(C)C=CC=CC=1>[O:45]=[C:44]1[CH2:43][CH2:42][C:41](=[O:46])[N:1]1[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]([CH2:12][C:13]1[CH:17]=[CH:16][S:15][CH:14]=1)[C:9](=[O:18])[CH:8]([NH:19][C:20](=[O:40])[C@H:21]([NH:26][C:27](=[O:39])[C:28]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:29])[CH3:30])[CH2:22][CH:23]([CH3:24])[CH3:25])[CH2:7]2

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 7922Succinic anhydrideHCID 517045Sodium AcetateHCID 59620329HCID 59620329, compound

Product 1

HCID 59620355HCID 59620355, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

tert-Butyl 1-((2R)-1-(8-amino-2-oxo-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-ylamino)-4-methyl-1-oxopentan-2-ylamino)-2-methyl-1-oxopropan-2-ylcarbamate (100 mg) and succinic anhydride (21 mg) were added to toluene (1 mL), and the mixture was refluxed for two hours while being stirred. The reaction mixture was concentrated under reduced pressure, and the thus-recovered residue was purified through silica gel column chromatography (ethyl acetate, chloroform:methanol (5:1)), whereby the Compound A (114 mg) was yielded. The Compound A (110 mg), sodium acetate (75 mg), and acetic anhydride (1 mL) were added to toluene (1 mL), and the mixture was stirred at 80° C. for 20 minutes. The mixture was cooled to room temperature, and water was added thereto. The mixture was extracted with ethyl acetate twice, and the organic layers were combined. The combined organic layer was dried over sodium sulfate, and the solvent was evaporated under reduced pressure, whereby the title compound (100 mg) was yielded.

Workup

  1. temperaturethe mixture was refluxed for two hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe thus-recovered residue was purified through silica gel column chromatography (ethyl acetate, chloroform:methanol (5:1)), whereby the Compound A (114 mg)
  4. customwas yielded
  5. stirringthe mixture was stirred at 80° C. for 20 minutes
  6. extractionThe mixture was extracted with ethyl acetate twice
  7. dry with materialThe combined organic layer was dried over sodium sulfate
  8. customthe solvent was evaporated under reduced pressure, whereby the title compound (100 mg)
  9. customwas yielded

Sources & evidence

ORD record
ord-cfd12f609f0b4484b88d8d3cb41086a9
Source dataset
uspto-grants-2012_10
Patent number
US08299255B2

Reaction notes

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