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

HRID 2110017노트

반응식

HRID 2110017 반응식
[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

참가 물질

7

반응물 4

HCID 962WaterHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 69070098HCID 69070098, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-dc18e1e762c148d899bb824362af408a
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07517875B2

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