4-Methylmorpholine → HCID 178471555、化合物

HRID 1494614

反応式

HRID 1494614 の反応式
[C:1]([NH:4][C:5]1[N:6]=[C:7]([OH:26])[C:8]2[CH:14]=[C:13]([CH:15]=[CH:16][C:17]3[CH:22]=[CH:21][C:20]([C:23](O)=[O:24])=[CH:19][CH:18]=3)[CH:12]=[N:11][C:9]=2[N:10]=1)(=[O:3])[CH3:2].CN1CCOCC1.C1(NP(Cl)(=O)OC2C=CC=CC=2)C=CC=CC=1.Cl.[NH2:52][C@H:53]([C:61]([O:63][CH2:64][CH3:65])=[O:62])[CH2:54][CH2:55][C:56]([O:58][CH2:59][CH3:60])=[O:57]>CN1CCCC1=O>[C:1]([NH:4][C:5]1[N:6]=[C:7]([OH:26])[C:8]2[CH:14]=[C:13]([CH:15]=[CH:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([NH:52][C@H:53]([C:61]([O:63][CH2:64][CH3:65])=[O:62])[CH2:54][CH2:55][C:56]([O:58][CH2:59][CH3:60])=[O:57])=[O:24])=[CH:19][CH:18]=3)[CH:12]=[N:11][C:9]=2[N:10]=1)(=[O:3])[CH3:2]

参加物

6

反応物 4

HCID 79724-MethylmorpholineHCID 73960Glutamic acid diethyl ester hydrochlorideHCID 103959Phosphoramidochloridic acid, N-phenyl-, phenyl esterHCID 178474467HCID 178474467、化合物

生成物 1

HCID 178471555HCID 178471555、化合物収率 66%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
0 °C

実験手順

To an ice cold solution of 1.5 g (0.0043 mol) of 2-acetamido-4-hydroxy-6-[2-(4-carboxyphenyl)ethenyl]pyrido[2,3-d]pyrimidine in 40 mL of N-methylpyrrolidone containing 1.4 mL of N-methylmorpholine was added 1.72 g (0.0064 mol) of phenyl N-phenylphosphoramidochloridate in a single portion. The resulting mixture was stirred at 0° C. for 30 minutes. Diethyl L-glutamate hydrochloride (1.53 g, 0.0064 mol) was then added and the reaction mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and the residual solid triturated with 50 mL of 1N aqueous sodium carbonate. The mixture was filtered and the collected solid dissolved in 20 mL of chloroform. The chloroform solution was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated to dryness and chromatographed on silica gel. Elution with chloroform:methanol (95:5) gave 1.52 g (66%) of the title compound, which may be alternatively named as diethyl 2-acetyl-5,10-dideaza-9,10-didehydrofolate, mp> 250° C.; NMR (CDCl3Me2SO-d6) delta 1.15-1.45 (2t, 6H, J=6 Hz), 2.0-2.65(m, 4H), 2.3(s, 3H), 4.0-4.35(2q, 4H, J=6 Hz), 4.5-4.75(m, 1H), 6.7, 6.9(AB q, 2H, J=15 Hz), 7.33, 7.84(AB q, 4H, J=9 Hz), 8.25-8.38(m, 2H), 8.62(d, 1H, J=2 Hz), 11.5-12.5(br, 2H); IR (Nujol) 3320, 3150, 1730, 1680, 1630, 1600 cm-1.

後処理

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residual solid triturated with 50 mL of 1N aqueous sodium carbonate
  4. filtrationThe mixture was filtered
  5. dissolutionthe collected solid dissolved in 20 mL of chloroform
  6. dry with materialThe chloroform solution was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness
  9. customchromatographed on silica gel
  10. washElution with chloroform:methanol (95:5)

出典と根拠

ORDレコード
ord-b329ae8f52224810806a772a4cf7ad9c
出典データセット
uspto-grants-1991_06
特許番号
US05026851

関連ノート

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