Triethylamine → HCID 57962249, 화합물

HRID 541831노트

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HRID 541831 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1.S(Cl)(Cl)=O.C(N(CC)CC)C.[N+:27]([C:30]1[CH:31]=[C:32]([CH2:36][C:37](O)=[O:38])[CH:33]=[CH:34][CH:35]=1)([O-:29])=[O:28]>C(Cl)Cl.O1CCCC1>[N+:27]([C:30]1[CH:31]=[C:32]([CH2:36][C:37]([NH:1][C:2]2[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH:5]=[CH:6][CH:7]=2)=[O:38])[CH:33]=[CH:34][CH:35]=1)([O-:29])=[O:28]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 158763-Nitrophenylacetic acidHCID 24386Thionyl ChlorideHCID 12877220tert-butyl N-(3-aminophenyl)carbamate

생성물 1

HCID 57962249HCID 57962249, 화합물수율 95.4%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

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온도
80 °C

실험 절차

tert-Butyl (3-aminophenyl)carbamate (1.0 g, 4.8 mmol) was dissolved in methylene chloride (4 mL) and then thionyl chloride (2.0 mL, 27 mmol) was added. The mixture was heated at 80° C. for 1 h. The solvent was removed under vacuum. Tetrahydrofuran (20 mL), triethylamine (2.3 mL, 17 mmol) and (3-nitrophenyl)acetic acid (0.87 g, 4.8 mmol) were then added and the mixture was stirred at rt for 1 h. The solvent was removed under vacuum and then EtOAc and water were added. The aqueous phase was extracted again with EtOAc. The organics were combined, dried over Na2SO4 and concentrated to give the desired product as a white powder (1.70 g, 95%). LCMS for C19H21N3O5 (M-tBu+H)+: m/z=316.0.

후처리

  1. customThe solvent was removed under vacuum
  2. customThe solvent was removed under vacuum
  3. additionEtOAc and water were added
  4. extractionThe aqueous phase was extracted again with EtOAc
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e2541d32f1104380a9192b61b1a40acb
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871753B2

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