Hydrochloric Acid → 4-[2-(5-Chloro-2-hydroxybenzoylamino)benzoylamino]butanoic acid

HRID 2374718

반응식

HRID 2374718 반응식
[NH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:5].C[Si](Cl)(C)C.C(N(CC)CC)C.[Cl:29][C:30]1[CH:31]=[CH:32][C:33]([OH:39])=[C:34]([CH:38]=1)[C:35](Cl)=[O:36].[OH-].[Na+].Cl>C(Cl)Cl>[Cl:29][C:30]1[CH:31]=[CH:32][C:33]([OH:39])=[C:34]([CH:38]=1)[C:35]([NH:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:5])=[O:36]

참가 물질

8

반응물 6

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 128632335-Chloro-2-hydroxybenzoyl chlorideHCID 134423754-(2-Aminobenzamido)butanoic acid

생성물 1

HCID 231185664-[2-(5-Chloro-2-hydroxybenzoylamino)benzoylamino]butanoic acid

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a suspension of 2.30 g (10.4 mmol) of 4-(2-aminobenzoylamino)butanoic acid in 40 ml of dry methylene chloride, add 9.56 g (88.50 mmol) of trimethylsilyl chloride and allow the reaction to reflux for 5 hours. Then place the flask in an ice bath and add 1.34 g (13.30 mmol) of triethylamine and a solution of 1.67 g (8.85 mmol) of 5-chloro-2-hydroxybenzoyl chloride dissolved in 5 ml of dry methylene chloride. Allow the reaction to stir for 30 minutes in an ice bath and 24 hours at room temperature. Eliminate the solvent at low pressure, add 30 ml of 10% NaOH to the crude product and continue stirring the mixture until the oil has completely disappeared. Immediately acidify with concentrated HCl, filter the resulting solid and wash several times with water and with ether. Purify the reaction product by recrystallization (EtOH/H2O). This yields 0.95 g (29%) of 4-[2-(5-chloro-2-hydroxybenzoylamino)benzoylamino]butanoic acid as a white solid.

후처리

  1. customthe reaction
  2. temperatureto reflux for 5 hours
  3. customthe reaction
  4. stirringcontinue stirring the mixture until the oil
  5. filtrationfilter the resulting solid
  6. washwash several times with water
  7. customPurify the reaction product
  8. customby recrystallization (EtOH/H2O)

출처 및 근거

ORD 기록
ord-133efa7cc3114b5d8a5d52402b5a2804
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07462735B2

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