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Acetic Acid → HCID 59556932, compound

HRID 1173601
Notes
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Reaction equation

HRID 1173601 reaction equation
C(NC(C)C)(C)C.[CH:8]1([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10][CH2:9]1.[CH3:18][C@H:19]1[C:23](=O)[O:22]C(=O)[N:20]1[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27].C(O)(=O)C>C1COCC1.O>[CH2:29]([O:28][C:26]([NH:20][C@@H:19]([CH3:18])[C:23]([C:8]1([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10][CH2:9]1)=[O:22])=[O:27])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7912DiisopropylamineHCID 11118442Phenylmethyl (4S)-4-methyl-2,5-dioxo-3-oxazolidinecarboxylateHCID 13676038tert-Butyl cyclopropanecarboxylate

Product 1

HCID 59556932HCID 59556932, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

A solution of diisopropylamine (0.740 mL) in THF (25 mL) was cooled to −78° C., n-butyllithium-hexane solution (3.26 mL, 1.6 mol/L) was added dropwise and, after the completion of the dropwise addition, the mixture was stirred at −78° C. for 1 hr. Subsequently, a solution of tert-butyl cyclopropanecarboxylate (0.800 g) in THF (5 mL) was added dropwise, and the mixture was further stirred at −78° C. for 30 min. A solution of benzyl(4S)-4-methyl-2,5-dioxo-1,3-oxazolidine-3-carboxylate (1.00 g) in THF (10 mL) was added dropwise at −78° C. over 10 min, and the mixture was further stirred at −78° C. for 30 min. Acetic acid (2.0 mL) was added to the reaction mixture and, after warming to room temperature, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→1/1) to give the title compound as a colorless oil (yield: 401 mg, 29%).

Workup

  1. additionn-butyllithium-hexane solution (3.26 mL, 1.6 mol/L) was added dropwise
  2. additionafter the completion of the dropwise addition
  3. stirringthe mixture was further stirred at −78° C. for 30 min
  4. stirringthe mixture was further stirred at −78° C. for 30 min
  5. temperatureafter warming to room temperature
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extract was washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→1/1)

Sources & evidence

ORD record
ord-b2d8249382f743b7b410c08da07f158c
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07834051B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes