Heptanoic Acid → N-(5-(tert-Butyldiphenylsilyloxy)pentyl)-N-isopropylheptanamide

HRID 1485814Notes

Reaction equation

HRID 1485814 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH:24][CH:25]([CH3:27])[CH3:26])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28](O)(=[O:35])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>>[Si:1]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24]([CH:25]([CH3:27])[CH3:26])[C:28](=[O:35])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 8094Heptanoic AcidHCID 708552025-(tert-Butyldiphenylsilyloxy)-N-isopropylpentan-1-amine

Product 1

HCID 70819093N-(5-(tert-Butyldiphenylsilyloxy)pentyl)-N-isopropylheptanamideYield 90.8%

Procedure

Following literature precedent,2 5-(tert-butyldiphenylsilyloxy)-N-isopropylpentan-1-amine (0.90 g, 2.30 mmol) was condensed with heptanoic acid (0.26 g, 2.0 mmol) to give the title amide (0.90 g, 79%) as a viscous oil. TLC:EtOAc/hexanes (3:8), Rf˜0.60; 1H NMR (300 MHz, 1:1 mixture of rotamers) δ 7.65-7.67 (m, 4H), 7.30-7.40 (m, 6H), 4.62-4.72 (m, 0.5 H), 4.00-4.80 (m, 0.5H), 3.62 (t, J=4.8 Hz, 1H), 3.68 (t, J=4.8 Hz, 1H), 3.02 (t, J=5.2 Hz, 1H), 3.16 (t, J=5.2 Hz, 1H), 2.38 (t, J=5.3 Hz, 1H), 2.24 (t, J=5.3 Hz, 1H), 1.50-1.68 (m, 6H), 1.26-1.44 (m, 8H), 1.18 (d, J=7.3 Hz 3H), 1,12, (d, J=7.3 Hz 3H), 1.03 (s, 4.5 H), 1.04 (s, 4.5H), 0.88 (t, J=7.3 Hz, 3H); 13C NMR (125 MHz) δ 173.38, 172.76, 135.80, 135.78, 134.36, 134.12, 129.85, 129.73, 127.88, 127.82, 64.22, 63.68, 48.43, 45.62, 43.64, 41.27, 34.13, 34.05, 32.61, 32.36, 31.96, 31.93, 31.51, 29.63, 29.47, 27.10, 27.03, 25.94, 25.78, 24.03, 23.77, 22.81, 21.63, 20.78, 19.47, 14.33, 14.28. HRMS calcd for C31H50NO2Si [M+1]+ 496.3611, found 496.3615.

Sources & evidence

ORD record
ord-17f4500cbd4b4d05b2bfc699888ccc05
Source dataset
uspto-grants-2016_08
Patent number
US09422318B2

Reaction notes

Loading…