Hydrochloric Acid → HCID 131727778, compound

HRID 2039509Notes

Reaction equation

HRID 2039509 reaction equation
C([CH:9]([C:19]([OH:21])=[O:20])[N:10]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:11][CH2:12][CH2:13][CH3:14])(=O)C1C=CC=CC=1.Cl.C(=O)(O)[O-].[Na+].[C:28](Cl)([O:30][CH2:31][CH:32]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:38]2[C:33]1=[CH:34][CH:35]=[CH:36][CH:37]=2)=[O:29]>O1CCOCC1.O>[C:28]([CH:9]([C:19]([OH:21])=[O:20])[N:10]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:11][CH2:12][CH2:13][CH3:14])([O:30][CH2:31][CH:32]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:38]2[C:33]1=[CH:34][CH:35]=[CH:36][CH:37]=2)=[O:29]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 343679-Fluorenylmethyl chloroformateHCID 516892Sodium BicarbonateHCID 66617053HCID 66617053, compound

Product 1

HCID 131727778HCID 131727778, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

10 mmol of compound (80) is dissolved in 30 mL of dioxane, and 10 mL of 6N hydrochloric acid solution is added, and the solution is refluxed overnight. The reaction is cooled to room temperature, concentrated to dryness, redissolved in 30 mL of tetrahydrofuran, and 10 mL of water and 30 mmol of sodium bicarbonate is added, followed by 15 mmol of Fmoc-Cl. The biphasic solution is stirred for 1 hour, and the tetrahydrofuran removed under vacuum. The aqueous solution is extracted with 1×50 mL of diethyl ether, acidified with 1N hydrochloric acid solution, and extracted with 2×50 mL of ethyl acetate. The ethyl acetate layers are combined, dry over sodium sulfate, and concentrated. Compound (81) is purified by silica gel column chromatography.

Workup

  1. temperaturethe solution is refluxed overnight
  2. concentrationconcentrated to dryness
  3. dissolutionredissolved in 30 mL of tetrahydrofuran
  4. customthe tetrahydrofuran removed under vacuum
  5. extractionThe aqueous solution is extracted with 1×50 mL of diethyl ether
  6. extractionextracted with 2×50 mL of ethyl acetate
  7. dry with materialdry over sodium sulfate
  8. concentrationconcentrated
  9. customCompound (81) is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1ac56ab132204eafb1508b28ecb5e72a
Source dataset
uspto-grants-2013_11
Patent number
US08580746B2

Reaction notes

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