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Acetic Anhydride → HCID 59620355, compound

HRID 1887775
Notes
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Reaction equation

HRID 1887775 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 962
Water
Solvent
HCID 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-e72bef38c1854d15bb1632091545548a
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08501772B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes