Tert-Butylamine → HCID 11613980, compound

HRID 1868588Notes

Reaction equation

HRID 1868588 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:28]=[C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:30]=1)[C:12]1[O:13][C:14]2[C:19]([C:20](=[O:22])[CH:21]=1)=[CH:18][CH:17]=[C:16]([O:23][CH2:24][CH:25]1[O:27][CH2:26]1)[CH:15]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:39]([NH2:43])([CH3:42])([CH3:41])[CH3:40]>CO>[C:39]([NH:43][CH2:26][CH:25]([OH:27])[CH2:24][O:23][C:16]1[CH:15]=[C:14]2[C:19]([C:20](=[O:22])[CH:21]=[C:12]([C:11]3[CH:28]=[C:29]([O:31][CH2:32][C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH:30]=[C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:10]=3)[O:13]2)=[CH:18][CH:17]=1)([CH3:42])([CH3:41])[CH3:40]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 76554795HCID 76554795, compound2×

Product 1

HCID 11613980HCID 11613980, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3′,5′-dibenzyloxy-7-(2,3-epoxy-propoxy)-flavone, 28 (2.5 g, 4.9 mmol) and tert-butyl amine (1.05 mL, 9.8 mmol) in dry methanol (150 mL) was stirred at reflux for 6 h. Reaction mixture was concentrated on rotavapor and crude product purified by column chromatography to afford 34. Yield 2.6 g (93%); mp 170-171° C.; MS (FAB) 580 (M++1); IR (KBr) 3428, 1648; 1H NMR (200 MHz, CDCl3) δ 8.02 (d, J=8.8 Hz, 1H), 7.59-7.33 (m, 10H), 7.13 (d, J=1.9 Hz, 2H), 7.07 (s, 1H), 7.01 (dd, J=9.8 Hz, 2.0 Hz, 1H), 6.76 (s, 1H), 6.71 (s, 1H), 5.12 (s, 4H), 4.57-4.54 (m, 1H), 4.27-4.16 (m, 2H), 3.24 (d, J=10.5 Hz, 1H), 3.05 (t, J=10.6 Hz, 1H), 1.45 (s, 9H); 13C NMR δ 178.3, 163.5, 163.2, 160.7, 158.1, 136.8, 133.9, 129.0, 128.6, 127.9, 127.5, 118.3, 115.2, 108.0, 105.9, 101.5, 72.9, 70.8, 67.5, 54.0, 45.3, 28.1. Analysis Calcd for C36H37NO6: C, 74.59; H, 6.43; N, 2.42. Found: C, 74.44; H, 6.35; N, 2.51.

Workup

  1. temperatureat reflux for 6 h
  2. customReaction mixture
  3. concentrationwas concentrated on rotavapor and crude product
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-682a6d131f31416e8025368f58587c7c
Source dataset
uspto-grants-2009_12
Patent number
US07635779B2

Reaction notes

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