Water → 4-Tert-butoxycarbonylamino-3-methylaminobenzoic acid methyl ester

HRID 2110017ノート

反応式

HRID 2110017 の反応式
[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[C:6]([N:18]([CH3:31])S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].C1(S)C=CC=CC=1.O>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12])=[C:6]([NH:18][CH3:31])[CH:5]=1

参加物

7

反応物 4

HCID 962WaterHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 69070098HCID 69070098、化合物

生成物 1

HCID 690638464-Tert-butoxycarbonylamino-3-methylaminobenzoic acid methyl ester

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

After dissolving 4-tert-butoxycarbonylamino-3-[methyl-(2-nitro-benzenesulfonyl)-amino]-benzoic acid methyl ester (1.41 g, 2.73 mmol) in dimethylformamide (10 ml), potassium carbonate (1.13 g, 8.16 mmol) and thiophenol (0.307 ml, 2.99 mmol) were added in an ice bath, and the mixture was stirred at room temperature for 1 hour. Water (100 ml) was added to the reaction mixture, and extraction was performed with ethyl acetate (40 ml×3 times). The obtained organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure was purified by silica gel column chromatography (n-hexane/ethyl acetate=85/15) to obtain 4-tert-butoxycarbonylamino-3-methylamino-benzoic acid methyl ester. The compound was identified by LC-MS. Yield: 794.3 mg (62.7%), [M+1]=281.1.

後処理

  1. additionwere added in an ice bath
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe residue obtained by concentration under reduced pressure
  5. customwas purified by silica gel column chromatography (n-hexane/ethyl acetate=85/15)

出典と根拠

ORDレコード
ord-dc18e1e762c148d899bb824362af408a
出典データセット
uspto-grants-2009_04
特許番号
US07517875B2

反応ノート

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