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

HRID 1060445ノート

反応式

HRID 1060445 の反応式
[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]

参加物

8

反応物 4

HCID 25517Ammonium ChlorideHCID 433294Lithium ChlorideHCID 21986264HCID 21986264、化合物HCID 22970630HCID 22970630、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

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)−.

後処理

  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

出典と根拠

ORDレコード
ord-45b20c6135474b9fa791904faf2bff14
出典データセット
uspto-grants-2003_02
特許番号
US06521666B1

反応ノート

読み込み中…