Water → HCID 178472471, compound

HRID 660137Notes

Reaction equation

HRID 660137 reaction equation
Cl[C:2](=[O:7])[C:3]([O:5][CH3:6])=[O:4].[NH2:8][C:9]1[CH:26]=[CH:25][C:12]([O:13][C@@H:14]2[CH2:19][CH2:18][C@H:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:16][CH2:15]2)=[CH:11][CH:10]=1.C(N(C(C)C)CC)(C)C.O>C(Cl)Cl>[CH3:6][O:5][C:3](=[O:4])[C:2]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([O:13][C@@H:14]2[CH2:19][CH2:18][C@H:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:16][CH2:15]2)=[CH:25][CH:26]=1)=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 79846Methyl chloroglyoxylateHCID 81531DiisopropylethylamineHCID 178472464HCID 178472464, compound

Product 1

HCID 178472471HCID 178472471, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl chlorooxoacetate (2.41 mL, 26.1 mmol) was added dropwise over 2 mins to a stirred solution of ethyl cis-4-(4-aminophenoxy)cyclohexanecarboxylate (6.24 g, 23.7 mmol) and diisopropylethylamine (8.25 mL, 47.4 mmol) in DCM (200 mL) and the reaction mixture was stirred at ambient temperature for 16 h. Water (75 mL) was added and the layers were separated. The organic layer was washed with an aqueous solution of hydrochloric acid (1M, 75 mL) and then a saturated aqueous solution of sodium hydrogen carbonate (75 mL), dried (MgSO4) and concentrated in vacuo to provide the title compound as a white solid (8.23 g, 100%).

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with an aqueous solution of hydrochloric acid (1M, 75 mL)
  3. dry with materiala saturated aqueous solution of sodium hydrogen carbonate (75 mL), dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5b3929b0677c4f669443ac8f96810225
Source dataset
uspto-grants-2011_12
Patent number
US08084478B2

Reaction notes

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