4-(3-(Tert-butoxy)-2-(4-nitrobenzamido)-3-oxopropyl)-2-methoxyphenyl 4-(heptyloxy)benzoate → 4-(2-(4-Aminobenzamido)-3-(tert-butoxy)-3-oxopropyl)-2-methoxyphenyl 4-(heptyloxy)benzoate

HRID 1889161ノート

反応式

HRID 1889161 の反応式
[CH2:1]([O:8][C:9]1[CH:46]=[CH:45][C:12]([C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([NH:31][C:32](=[O:42])[C:33]3[CH:38]=[CH:37][C:36]([N+:39]([O-])=O)=[CH:35][CH:34]=3)[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:18][C:17]=2[O:43][CH3:44])=[O:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]>[Pd]>[CH2:1]([O:8][C:9]1[CH:46]=[CH:45][C:12]([C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([NH:31][C:32](=[O:42])[C:33]3[CH:38]=[CH:37][C:36]([NH2:39])=[CH:35][CH:34]=3)[C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])=[CH:18][C:17]=2[O:43][CH3:44])=[O:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

参加物

3

反応物 1

HCID 585458734-(3-(Tert-butoxy)-2-(4-nitrobenzamido)-3-oxopropyl)-2-methoxyphenyl 4-(heptyloxy)benzoate

生成物 1

HCID 585456494-(2-(4-Aminobenzamido)-3-(tert-butoxy)-3-oxopropyl)-2-methoxyphenyl 4-(heptyloxy)benzoate収率 73%

試薬・触媒・溶媒 1

HCID 23938Palladium触媒

実験手順

Prepared using General Procedure 9: A stirred solution of 4-(3-(tert-butoxy)-2-(4-nitrobenzamido)-3-oxopropyl)-2-methoxyphenyl 4-(heptyloxy)benzoate INT-8 (1.70 g, 2.68 mmol) in THF (30 mL) was degassed under N2 flow. Pd/C (10 wt % 0.17 g, 0.16 mmol) was added and the suspension was degassed under N2 flow. The reaction vessel was flushed with hydrogen gas and the reaction was stirred under an atmosphere of hydrogen overnight. The reaction was diluted with THF (10 mL) and filtered over celite. The material was concentrated and purified by chromatography (EA/hexanes) to afford 1.20 g (73%) of 4-(2-(4-aminobenzamido)-3-(tert-butoxy)-3-oxopropyl)-2-methoxyphenyl 4-(heptyloxy)benzoate INT-9. LCMS-ESI (m/z) calculated for C35H44N2O7: 604; found 605 [M+H]+, tR=3.15 min (Method 4). 1H NMR (400 MHz, DMSO) δ 8.24-8.18 (d, J=7.8 Hz, 1H), 8.05-7.94 (m, 2H), 7.61-7.52 (m, 2H), 7.13-7.04 (m, 4H), 6.93-6.85 (m, 1H), 6.57-6.48 (m, 2H), 5.65 (s, 2H), 4.58-4.50 (m, 1H), 4.12-4.03 (t, J=6.5 Hz, 2H), 3.71 (s, 3H), 3.16-3.03 (m, 2H), 1.79-1.69 (m, 2H), 1.47-1.23 (m, 17H), 0.90-0.82 (m, 3H).

後処理

  1. customPrepared
  2. custom(1.70 g, 2.68 mmol) in THF (30 mL) was degassed under N2 flow
  3. customthe suspension was degassed under N2 flow
  4. customThe reaction vessel was flushed with hydrogen gas
  5. additionThe reaction was diluted with THF (10 mL)
  6. filtrationfiltered over celite
  7. concentrationThe material was concentrated
  8. custompurified by chromatography (EA/hexanes)

出典と根拠

ORDレコード
ord-489c6b9382d24a6094da44785c93ce10
出典データセット
uspto-grants-2013_08
特許番号
US08501982B2

反応ノート

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