Ammonium Hydroxide → HCID 66722704, compound

HRID 1639532Notes

Reaction equation

HRID 1639532 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[C:19]([OH:21])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC2N(O)N=[N:28]C=2C=1.C(N=C=NCCCN(C)C)C.[OH-].[NH4+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[C:19](=[O:21])[NH2:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 66722684HCID 66722684, compound

Product 1

HCID 66722704HCID 66722704, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.5 gm (5.2 mmol) of methyl 4-benzyloxy-3-carboxybenzoate in 8 mL of DMF is added 0.85 gm (6.2 mmol) of HOBT and 1.2 gm (6.2 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC). After 1 hr, 0.86 mL of 30% ammonium hydroxide is added, and the solution stirred for an additional 2 hr. The reaction mixture is concentrated to remove most of the DMF, and the residue is taken up in ethyl acetate. The ethyl acetate solution is washed with brine and dried over Na2SO4. Removal of solvent by rotoevaporation gives 1.37 gm (4.8 mmol) of methyl 4-benzyloxy-3-carbamoylbenzoate.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customto remove most of the DMF
  3. washThe ethyl acetate solution is washed with brine
  4. dry with materialdried over Na2SO4
  5. customRemoval of solvent by rotoevaporation

Sources & evidence

ORD record
ord-91672ebaa4c447ba80fc0de360d6ee39
Source dataset
uspto-grants-2012_02
Patent number
US08110570B2

Reaction notes

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