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

HRID 1626722ノート

反応式

HRID 1626722 の反応式
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]

参加物

7

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 189451333-(Furan-3-yl)benzoic acidHCID 66680776Methyl 2-[(4-aminobutanoyl)amino]-5-chlorobenzoate hydrochloride

生成物 1

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

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 31374Dimethylacetamide溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-e051d01ad0a54e3593eac4ad335dd754
出典データセット
uspto-grants-2014_07
特許番号
US08785473B2

反応ノート

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