Ammonium Chloride → N-(2,6-dichlorobenzoyl)-4-(2-cyano-3-thienyl)-L-phenylalanine methyl ester

HRID 24673노트

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HRID 24673 반응식
[CH3:1][O:2][C:3](=[O:31])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20](OS(C(F)(F)F)(=O)=O)=[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[Sn](C)(C)[C:34]1[CH:38]=[CH:37][S:36][C:35]=1[C:39]#[N:40].[Li+].[Cl-].[NH4+].[Cl-]>O1CCOCC1.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3](=[O:31])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:34]2[CH:38]=[CH:37][S:36][C:35]=2[C:39]#[N:40])=[CH:19][CH:18]=1)[NH:5][C:6](=[O:15])[C:7]1[C:8]([Cl:14])=[CH:9][CH:10]=[CH:11][C:12]=1[Cl:13]

참가 물질

8

반응물 4

HCID 25517Ammonium ChlorideHCID 433294Lithium ChlorideHCID 21986264HCID 21986264, 화합물HCID 22970630HCID 22970630, 화합물

생성물 1

HCID 53922803N-(2,6-dichlorobenzoyl)-4-(2-cyano-3-thienyl)-L-phenylalanine methyl ester수율 38%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

A mixture of N-(2,6-dichlorobenzoyl)-O-(trifluoromethane sulfonyl)-L-tyrosine methyl ester (361 mg), trimethyl(2-cyano-3-thienyl)tin (393 mg), Pd(PPh3)4 (42 mg) and LiCl (93 mg) in dioxane (8 mL) was stirred at 100° C. under N2 for 38 h. The mixture was diluted with AcOEt and treated with 10% NH4Cl aqueous solution (6 mL). After stirring at room temperature for 1 h, the mixture was filtered through Celite and washed with AcOEt. The combined organic layers were washed successively with water and brine, dried (MgSO4) and evaporated under reduced pressure. The residue was purified by silica gel chromatography to afford N-(2,6-dichlorobenzoyl)-4-(2-cyano-3-thienyl)-L-phenylalanine methyl ester (126 mg). ESMS m/z 481 (M++Na), 459 (MH+), 457 (M−H)−.

후처리

  1. stirringAfter stirring at room temperature for 1 h
  2. filtrationthe mixture was filtered through Celite
  3. washwashed with AcOEt
  4. washThe combined organic layers were washed successively with water and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure
  7. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-5e08f58803cd4e678e8059227ae87f74
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855843B2

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