Water → HCID 86607498, compound

HRID 898852Notes

Reaction equation

HRID 898852 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:13]([O:17][C:18]([C@@:20]1([NH:33]C(OC(C)(C)C)=O)[CH2:22][C@@:21]1([CH2:29][N:30]=[N+:31]=[N-:32])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C(OC([C@@]1(NC(OC(C)(C)C)=O)C[C@]1(CO)C1C=CC=CC=1)=O)(C)(C)C.O>C(#N)C>[C:13]([O:17][C:18]([C@@:20]1([NH2:33])[CH2:22][C@@:21]1([CH2:29][N:30]=[N+:31]=[N-:32])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 67525593HCID 67525593, compoundHCID 86607499HCID 86607499, compound

Product 1

HCID 86607498HCID 86607498, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

p-Toluenesulfonic acid monohydrate (5.2 g, 27 mmol) was added to a solution of the crude product (5.0 g) of (1R*,2S*)-2-azidomethyl-1-t-butoxycarbonylamino-2-phenyl-cyclopropanecarboxylic acid t-butyl ester, which was made from (1R*,2S*)-1-t-butoxycarbonylamino-2-hydroxymethyl-2-phenyl-cyclopropanecarboxylic acid t-butyl ester obtained in Preparation Example 2-6 by general method step 5-3, in acetonitrile (40 mL). The mixture was stirred at room temperature for 14 hours. After water (16 mL) was added, the mixture was further stirred for 7 hours and separated into layers by adding ethyl acetate (50 mL). The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution (30 mL), water (30 mL) and saturated aqueous sodium chloride solution (50 mL), and dried over sodium sulfate. The residue was filtrated and the solvent was evaporated to give a crude product of the title compound (2.8 g). The obtained product was used in the next step without further purification.

Workup

  1. stirringthe mixture was further stirred for 7 hours
  2. customseparated into layers
  3. additionby adding ethyl acetate (50 mL)
  4. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution (30 mL), water (30 mL) and saturated aqueous sodium chloride solution (50 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationThe residue was filtrated
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-7c43ea6e3b3c4f2d966591aefcad706e
Source dataset
uspto-grants-2008_04
Patent number
US07351825B2

Reaction notes

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