1-Hydroxybenzotriazole → Methyl 5-chloro-2-{[4-({[3-(furan-3-yl)phenyl]carbonyl}amino)butanoyl]amino}benzoate

HRID 1626722Notes

Reaction equation

HRID 1626722 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][C:6]([NH:8][C:9]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])=[O:7].[O:20]1[CH:24]=[CH:23][C:22]([C:25]2[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=2)[C:28](O)=[O:29])=[CH:21]1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C(=O)C.C(OCC)(=O)C>[Cl:19][C:16]1[CH:17]=[CH:18][C:9]([NH:8][C:6](=[O:7])[CH2:5][CH2:4][CH2:3][NH:2][C:28]([C:27]2[CH:31]=[CH:32][CH:33]=[C:25]([C:22]3[CH:23]=[CH:24][O:20][CH:21]=3)[CH:26]=2)=[O:29])=[C:10]([CH:15]=1)[C:11]([O:13][CH3:14])=[O:12]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18945133HCID 18945133, compoundHCID 66680776Methyl 2-[(4-aminobutanoyl)amino]-5-chlorobenzoate hydrochloride

Product 1

HCID 66679856Methyl 5-chloro-2-{[4-({[3-(furan-3-yl)phenyl]carbonyl}amino)butanoyl]amino}benzoateYield 85%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

1.00 g (3.3 mmol) of methyl 2-[(4-aminobutanoyl)amino]-5-chlorobenzoate hydrochloride, 0.61 g (3.3 mmol) of 3-(furan-3-yl)benzoic acid, 0.75 g (3.9 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, and 0.53 g (3.9 mmol) of 1-hydroxybenzotriazole were stirred in 10 mL of N,N-dimethylacetamide (DMAc) for 2 hours. After the completion of the reaction, ethyl acetate was added, and the mixture was diluted and washed with saturated sodium bicarbonate solution and saturated saline. After the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The obtained crude product was recrystallized using a mixed solvent of ethyl acetate and n-hexane, thereby giving 1.22 g of methyl 5-chloro-2-{[4-({[3-(furan-3-yl)phenyl]carbonyl}amino)butanoyl]amino}benzoate (yield: 85%).

Workup

  1. additionwas added
  2. additionthe mixture was diluted
  3. washwashed with saturated sodium bicarbonate solution and saturated saline
  4. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained crude product
  7. customwas recrystallized

Sources & evidence

ORD record
ord-e051d01ad0a54e3593eac4ad335dd754
Source dataset
uspto-grants-2014_07
Patent number
US08785473B2

Reaction notes

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