Sodium Hydroxide → HCID 67524770, compound

HRID 898851Notes

Reaction equation

HRID 898851 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:13]([O:17][C:18]([C@@:20]1([NH:30]C(OC(C)(C)C)=O)[C@@H:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C@H:21]1[CH3:29])=[O:19])([CH3:16])([CH3:15])[CH3:14].[OH-].[Na+]>C(#N)C>[C:13]([O:17][C:18]([C@@:20]1([NH2:30])[C@@H:22]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C@H:21]1[CH3:29])=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrateHCID 67524570HCID 67524570, compound

Product 1

HCID 67524770HCID 67524770, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Under argon atmosphere, p-toluenesulfonic acid monohydrate (3.5 g, 18 mmol) was added to a solution of (1S,2R,3R)-1-t-butoxycarbonylamino-2-methyl-3-phenyl-cyclopropanecarboxylic acid t-butyl ester (3.2 g, 9.1 mmol) obtained in Preparation Example 5-2 in acetonitrile (30 mL) at 0° C., and the mixture was stirred at room temperature for 16 hours. The obtained solution was cooled to 0° C., and 1N aqueous sodium hydroxide solution (20 mL) was added. The aqueous layer was extracted twice with ethyl acetate (15 mL) and dried over magnesium sulfate. Then, the residue was filtrated and the solvent was evaporated to give a crude product of the title compound (1.8 g, yield 99%) as a crude product of a pale-yellow oil. The obtained product was used in the next step without purification.

Workup

  1. temperatureThe obtained solution was cooled to 0° C.
  2. extractionThe aqueous layer was extracted twice with ethyl acetate (15 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationThen, the residue was filtrated
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-8bb1e9483a0444afaa1fb2bb6e1d7f89
Source dataset
uspto-grants-2008_04
Patent number
US07351825B2

Reaction notes

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