Benzaldehyde → (Z)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]-6-methylbenzoyl]amino]-3-phenylpropenoic acid methyl ester

HRID 1058423ノート

反応式

HRID 1058423 の反応式
CN(C)C(N(C)C)=N.[CH3:9][O:10][C:11](=[O:41])[CH:12](P(OC)(OC)=O)[NH:13][C:14](=[O:34])[C:15]1[C:20]([CH3:21])=[CH:19][C:18]([C:22]([NH:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28](O)[CH:27]=2)=[O:23])=[CH:17][C:16]=1[Cl:33].[CH:42](=O)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.[O:50]1CCCC1>>[CH3:9][O:10][C:11](=[O:41])/[C:12](/[NH:13][C:14](=[O:34])[C:15]1[C:20]([CH3:21])=[CH:19][C:18]([C:22]([NH:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([OH:50])[CH:27]=2)=[O:23])=[CH:17][C:16]=1[Cl:33])=[CH:42]/[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

参加物

5

反応物 4

HCID 240BenzaldehydeHCID 8028TetrahydrofuranHCID 664601,1,3,3-TetramethylguanidineHCID 23560749Rac.-n-[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]-6-methylbenzoyl]-2-(dimethoxyphosphinyl)glycine methyl ester

生成物 1

HCID 59918708(Z)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]-6-methylbenzoyl]amino]-3-phenylpropenoic acid methyl ester収率 73%

実験手順

1,1,3,3-Tetramethylguanidine (20 μL, 0.16 mmol) was added to a solution of rac.-N-[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]-6-methylbenzoyl]-2-(dimethoxyphosphinyl)glycine methyl ester (Example 132; 33 mg, 0.066 mmol) in tetrahydrofuran (1 mL) at room temperature. After 5 min, benzaldehyde (7 μL, 0.068 mmol) was added and the solution was stirred at room temperature for 16 h. The solvent was evaporated and the residue was purified by chromatography over silica gel. The column was eluted sequentially with chloroform, chloroform/methanol/water/acetic acid (600:30:10:6), chloroform/methanol/water/acetic acid (300:30:10:6) and chloroform/methanol/water/acetic acid (150:30:10:6). The appropriate fractions were combined and lyophilized to fuirnish (Z)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]-6-methylbenzoyl]amino]-3-phenylpropenoic acid methyl ester (23 mg, 73% yield).

後処理

  1. customThe solvent was evaporated
  2. customthe residue was purified by chromatography over silica gel
  3. washThe column was eluted sequentially with chloroform, chloroform/methanol/water/acetic acid (600:30:10:6), chloroform/methanol/water/acetic acid (300:30:10:6) and chloroform/methanol/water/acetic acid (150:30:10:6)

出典と根拠

ORDレコード
ord-21ea2983cd844e279a4e86c696556c75
出典データセット
uspto-grants-2003_02
特許番号
US06515124B2

反応ノート

読み込み中…