Dichloromethane → tert-Butyl 4-[N-[2-Acetoxymethyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]amino]benzoate

HRID 47860

反応式

HRID 47860 の反応式
[C:1]([O:4][CH2:5][C:6]1[N:15]([CH2:16][O:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[C:14](=[O:24])[C:13]2[C:8](=[CH:9][C:10]3[CH2:27][CH2:26][C:25](=O)[C:11]=3[CH:12]=2)[N:7]=1)(=[O:3])[CH3:2].ClCCl.[NH2:32][C:33]1[CH:45]=[CH:44][C:36]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[CH:35][CH:34]=1.[B][B][B][B][B][B][B][B][B][B]>CO>[C:1]([O:4][CH2:5][C:6]1[N:15]([CH2:16][O:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[C:14](=[O:24])[C:13]2[C:8](=[CH:9][C:10]3[CH2:27][CH2:26][CH:25]([NH:32][C:33]4[CH:45]=[CH:44][C:36]([C:37]([O:39][C:40]([CH3:41])([CH3:42])[CH3:43])=[O:38])=[CH:35][CH:34]=4)[C:11]=3[CH:12]=2)[N:7]=1)(=[O:3])[CH3:2]

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 233272Benzoic acid, 4-amino-, 1,1-dimethylethyl esterHCID 227442802-Acetoxymethyl-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-4,6-dioneHCID 178419135HCID 178419135、化合物

生成物 1

HCID 22744292tert-Butyl 4-[N-[2-Acetoxymethyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]amino]benzoate収率 63%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

2-Acetoxymethyl-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-4,6-dione (0.140 g, 0.36 mmol) was suspended in anhydrous methanol (8 ml) and then anhydrous dichoromethane (4 ml) was added until a clear solution was obtained. Tert-butyl 4-aminobenzoate (0.084 g, 0.44 mmol) was then added followed by decaborane (0.014 g, 0.12 mmol). The reaction mixture was stirred overnight at room temperature under argon. The solvent was removed in vaciio, and the residue was purified by column chromatography on elution with 40% ethyl acetate in hexane. The product was obtained as a glass (0.127 g, 63%) 1H-NMR (CDCl3) 1.20 (s, 9H, POM C(CH3)3), 1.58 (s, 9H, CO2C(CH3)3), 2.20 (s, 3H, CH3CO), 2.02, 2.72 (2×m, 2H, 7-CH2), 3.13 (m, 2H, 8-CH2), 4.36 (d, J=7.7 Hz, 1H, NH), 5.15 (q, J=6.8 Hz, 1H, 6-H), 5.21 (s, 2H, 2-CH2), 6.12 (AB system, J=10.7 Hz, 2H, POM CH2), 6.67 (d, J=8.8 Hz, 2H, 3,5′-ArH), 7.57 (s, 1H, 9-H), 7.85 (d, J=8.9 Hz, 2H, 2′,6′-ArH), 8.25 (s, 1H, 5-H); MS (ESI, m/z) 564 (M+H)+.

後処理

  1. customwas obtained
  2. customThe solvent was removed in vaciio
  3. customthe residue was purified by column chromatography on elution with 40% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-f03d6aa238fc40688ad833f92817bec1
出典データセット
uspto-grants-2004_03
特許番号
US06699861B1

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