Water → HCID 69886855, compound

HRID 1245301Notes

Reaction equation

HRID 1245301 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[NH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(OC([N:19]1[C:24](=[O:25])[CH:23]2[CH:21]([CH:22]2[C:26]([O-:28])=[O:27])[CH:20]1[C:29]([O-:31])=[O:30])=O)(C)(C)C.O>C(Cl)Cl>[C:26]([CH:22]1[CH:23]([C:24]([NH:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:25])[CH:21]1[CH:20]([C:29]([OH:31])=[O:30])[NH2:19])([OH:28])=[O:27]

Participants

6

Reactant 4

HCID 962WaterHCID 6115AnilineHCID 6451240Aluminum(III) ChlorideHCID 21911181HCID 21911181, compound

Product 1

HCID 69886855HCID 69886855, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of AlCl3 (53.8 mg, 0.40 mmol) in dry CH2Cl2 (1 mL) at 0° C., aniline (70 μl, 0.77 mmol) in CH2Cl2 (0.5 mL) was added dropwise. The mixture was stirred at room temperature for 10 min, and then ethyl (1SR, 2 SR, 5RS, 6RS) 3-tert-butoxycarbonyl-4-oxo-3-azabicyclo[3.1.0)hexane-2,6-dicarboxylate (106 mg 0.31 mmol) in dry CH2Cl2 (0.5 mL) was added. After stirring at room temperature for 4 h, a mixture of ice and water was added. The layers were separated and the aqueous phase was extracted with CH2Cl2 (X3). The combined organic layers were dried over MgSO4 and the solvent removed under reduced pressure. The residue was purified by flash chromatography (hexane/ethyl acetate 1/1) to give 67.5 mg of the desired compound (50% yield).

Workup

  1. stirringAfter stirring at room temperature for 4 h
  2. additionwas added
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with CH2Cl2 (X3)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. customthe solvent removed under reduced pressure
  7. customThe residue was purified by flash chromatography (hexane/ethyl acetate 1/1)

Sources & evidence

ORD record
ord-f413fa3ad2b6429db03c95b80bed221c
Source dataset
uspto-grants-2006_10
Patent number
US07125871B2

Reaction notes

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