Citric Acid → HCID 90060333, compound

HRID 1779255Notes

Reaction equation

HRID 1779255 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:19][C:20]([C@@H:22](/[CH:35]=[CH:36]/[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43](=[O:51])[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[C@@:23]([OH:34])([CH2:31][CH2:32][OH:33])[C:24]([O:26]C(C)(C)C)=[O:25])=[O:21])[C:14](=[O:18])[N:15]([CH3:17])[CH3:16])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].C(OC1C(OC(=O)C)=C(I)C=CC=1)(=[O:54])C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(#N)C.O>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:19][C:20]([C@H:22]([C@@:23]([OH:34])([CH2:31][C:32]([OH:33])=[O:54])[C:24]([OH:26])=[O:25])/[CH:35]=[CH:36]/[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43](=[O:51])[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])=[O:21])[C:14](=[O:18])[N:15]([CH3:16])[CH3:17])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4]

Participants

6

Reactant 3

HCID 311Citric AcidHCID 21865429Bis(acetoxy)iodobenzeneHCID 90060424HCID 90060424, compound

Product 1

HCID 90060333HCID 90060333, compoundYield 48.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

tert-Butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-dimethylcarbamoyl-ethylcarbamoyl]-2-hydroxy-2-(2-hydroxy-ethyl)-12-oxo-nonadec-4-enoate (96.8 mg, 0.133 mmol) was dissolved in acetonitrile (2.0 mL) and water (0.6 mL), and 4-acetamide-2,2,6,6-tetramethylpiperidine-1-oxyl (4.3 mg, 19.9 μmol) and diacetoxyiodobenzene (85.7 mg, 0.266 mmol) were added. The mixture was stirred at room temperature for 4 hours. An aqueous solution of citric acid was added to the reaction mixture, which was followed by extraction with ethyl acetate. The organic extract was washed with sodium thiosulfate and a saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was dissolved in formic acid (4.0 mL) and the mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified with preparative HPLC to obtain the title compound (43.2 mg).

Workup

  1. extractionwas followed by extraction with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with sodium thiosulfate
  4. dry with materiala saturated brine, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe resulting residue was dissolved in formic acid (4.0 mL)
  7. stirringthe mixture was stirred at room temperature for 5 hours
  8. concentrationThe reaction mixture was concentrated under reduced pressure
  9. customThe resulting residue was purified with preparative HPLC

Sources & evidence

ORD record
ord-69fa34367a794e6bafc8c6934354437a
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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