Citric Acid → HCID 90060310, compound

HRID 1779220Notes

Reaction equation

HRID 1779220 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][C@:9]([OH:59])([C@@H:17]([C:38](=[O:58])[NH:39][C@H:40]([C:53]([O:55][CH2:56][CH3:57])=[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:59])([CH2:8][CH2:7][OH:6])[C:10]([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11])=[O:58])[C:53]([O:55][CH2:56][CH3:57])=[O:54])=[CH:47][CH:46]=1)[C:50]#[C:51][CH3:52]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 5234Sodium ChlorideHCID 90060340HCID 90060340, compound

Product 1

HCID 90060310HCID 90060310, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

tert-Butyl (E)-(2S,3S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-ethoxycarbonyl-ethylcarbamoyl]-11-(2-heptyl-[1,3]dioxolan-2-yl)-2-hydroxy-undec-4-enoate (3.92 g, 4.49 mmol) was dissolved in acetonitrile (43 mL), and an aqueous solution of 0.5 M citric acid (19 mL, 9.50 mmol) was then added. The mixture was then stirred at 60° C. for 2.5 hours. The reaction solution was cooled to room temperature, and a mixture of a saturated aqueous solution (3.0 mL) of sodium chloride and water (60 mL) was then added. The solution was extracted three times with 20% ethyl acetate/n-hexane (32 mL). The organic layers were combined, then washed twice with a saturated aqueous solution (32 mL) of sodium chloride, dried over anhydrous sodium sulfate, and filtered. The solvent was then distilled off under reduced pressure to obtain 3.24 g (4.54 mmol, quant) of No. 5328627.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. additionwas then added
  3. extractionThe solution was extracted three times with 20% ethyl acetate/n-hexane (32 mL)
  4. washwashed twice with a saturated aqueous solution (32 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. customto obtain 3.24 g (4.54 mmol, quant) of No

Sources & evidence

ORD record
ord-d3f35dceffd34ca28df722eafe6aed4e
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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