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Citric Acid → HCID 90060183, compound

HRID 1779155
Notes
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Reaction equation

HRID 1779155 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][C@:9]([OH:58])([C@@H:17]([C:38](=[O:57])[NH:39][C@H:40]([C:53]([O:55][CH3:56])=[O:54])[CH2:41][C:42]1[CH:47]=[CH:46][C:45]([O:48][CH2:49][C:50]#[C:51][CH3:52])=[CH:44][CH:43]=1)/[CH:18]=[CH:19]/[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]1([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])OCC[O:27]1)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])(C)(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[Cl-].[Na+].O>C(#N)C>[CH2:49]([O:48][C:45]1[CH:44]=[CH:43][C:42]([CH2:41][C@H:40]([NH:39][C:38]([C@@H:17](/[CH:18]=[CH:19]/[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26](=[O:27])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C@@:9]([OH:58])([CH2:8][CH2:7][OH:6])[C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])=[O:57])[C:53]([O:55][CH3:56])=[O:54])=[CH:47][CH:46]=1)[C:50]#[C:51][CH3:52]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 5234Sodium ChlorideHCID 123758623HCID 123758623, compound

Product 1

HCID 90060183HCID 90060183, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Conditions

Temperature
60 °C

Procedure

No. 5327507 Compound C (50.8 g, 59.2 mmol) was dissolved in acetonitrile (560 mL), and then an aqueous solution of 0.5 M citric acid (249 mL, 125 mmol) was added to the solution, which was stirred at 60° C. for 2.5 hours. After confirming that inner temperature had returned to room temperature, a mixture of a saturated aqueous solution of sodium chloride (51 mL) and water (813 mL) was added. The solution was extracted with 20% ethyl acetate/n-hexane (457 mL) 3 times. The organic layers were combined, then washed twice with a saturated aqueous solution (230 mL) of sodium chloride, dried over anhydrous sodium sulfate, and filtered. The solvent was then distilled off under reduced pressure and the residue was purified on Biotage (silica gel, n-hexane/acetone) to obtain 23.6 g (33.7 mmol, 57% yield) of No. 5217614 (Compound D).

Workup

  1. customhad returned to room temperature
  2. additionwas added
  3. extractionThe solution was extracted with 20% ethyl acetate/n-hexane (457 mL) 3 times
  4. washwashed twice with a saturated aqueous solution (230 mL) of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. distillationThe solvent was then distilled off under reduced pressure
  8. customthe residue was purified on Biotage (silica gel, n-hexane/acetone)
  9. customto obtain 23.6 g (33.7 mmol, 57% yield) of No

Sources & evidence

ORD record
ord-94dc608ce1ab4bcab559c6a35a8593fa
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09266853B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes