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 2410646노트

반응식

HRID 2410646 반응식
[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]

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 23938Palladium촉매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-0aae8600928d40aa8d711b3cabfe1ca4
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08816121B2

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