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Ammonium Hydroxide → N-(2,6-dichlorobenzoyl)-4-(2-carbamoylphenyl)-L-phenylalanine methyl ester

HRID 1060422
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HRID 1060422 반응식
[CH3:1][O:2][C:3](=[O:32])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29](O)=[O:30])=[CH:19][CH:18]=1)[NH:5][C:6](=[O:15])[C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:14].C(N1C=CN=C1)([N:35]1C=CN=C1)=O.[OH-].[NH4+]>C1COCC1>[CH3:1][O:2][C:3](=[O:32])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29](=[O:30])[NH2:35])=[CH:19][CH:18]=1)[NH:5][C:6](=[O:15])[C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:14]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 53640164N-(2,6-dichlorobenzoyl)-4-(2-carboxyphenyl)-L-phenylalanine methyl ester

생성물 1

HCID 54317495N-(2,6-dichlorobenzoyl)-4-(2-carbamoylphenyl)-L-phenylalanine methyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

N-(2,6-dichlorobenzoyl)-4-(2-carboxyphenyl)-L-phenylalanine methyl ester (52.6 mg) was dissolved in anhydrous THF (1 mL), carbonyldiimidazole (36.1 mg) was added and the mixture was stirred at room temperature under N2 for 2 h. Ammonium hydroxide (29% aqueous solution, 135 μL) was added and the mixture was stirred for an additional 22 h. The mixture was then extracted with EtOAc. The extract was washed with 1N HCl, sat. NaHCO3 and brine, dried (MgSO4) and evaporated. The residue was purified through a silica gel column using toluene/EtOAc (1:1) as an eluent to give N-(2,6-dichlorobenzoyl)-4-(2-carbamoylphenyl)-L-phenylalanine methyl ester (48.1 mg. ESMS: m/z 471 (MH+).

후처리

  1. stirringthe mixture was stirred for an additional 22 h
  2. extractionThe mixture was then extracted with EtOAc
  3. washThe extract was washed with 1N HCl, sat. NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified through a silica gel column

출처 및 근거

ORD 기록
ord-19b4d02d7a334db288ac67ae0880c765
출처 데이터셋
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06521666B1

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