1-Adamantanecarboxylic acid → HCID 24888213, compound

HRID 1469972Notes

Reaction equation

HRID 1469972 reaction equation
[C:1]12([C:11](O)=[O:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.Br.[O:15]1[C:20]2[CH:21]=[CH:22][CH:23]=[C:24]([O:25][CH2:26][CH2:27][N:28]3[C:32]([CH3:33])=[C:31]([CH3:34])[S:30][C:29]3=[NH:35])[C:19]=2[O:18][CH2:17][CH2:16]1>>[O:15]1[C:20]2[CH:21]=[CH:22][CH:23]=[C:24]([O:25][CH2:26][CH2:27][N:28]3[C:32]([CH3:33])=[C:31]([CH3:34])[S:30][C:29]3=[N:35][C:11]([C:1]34[CH2:8][CH:7]5[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]5)[CH2:2]3)[CH2:10]4)=[O:12])[C:19]=2[O:18][CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 132351-Adamantanecarboxylic acidHCID 66858466HCID 66858466, compound

Product 1

HCID 24888213HCID 24888213, compoundYield 195.6%

Procedure

Adamantane-1-carboxylic acid (0.78 g, 0.12 mmol) and the product of Example 81A (0.15 g, 0.39 mmol) were processed according to the method of Example 77B. Purification by column chromatography (SiO2, 0-15% methanol/methylene chloride gradient) afforded 0.11 g (60%) of the title compound. 1H NMR (CDCl3, 300 MHz) δ ppm 1.68-1.79 (m, 6H), 1.96 (d, J=2.4 Hz, 6H), 2.04 (d, J=5.4 Hz, 3H), 2.17 (s, 3H), 2.29 (s, 3H), 4.18-4.30 (m, 4H), 4.36 (t, J=5.3 Hz, 2H), 4.51 (s, 2H), 6.44-6.58 (m, 2H), 6.72 (t, J=8.1 Hz, 1H); MS (DCI/NH3) m/z 469 (M+H)+. Anal. Calculated for C26H32N2O4S: C, 66.64; H, 6.88; N, 5.98. Found: C, 66.36; H, 6.80; N, 5.87.

Workup

  1. customPurification by column chromatography (SiO2, 0-15% methanol/methylene chloride gradient)

Sources & evidence

ORD record
ord-9a946b7eaad2434bb5f6a301ddf8aa49
Source dataset
uspto-grants-2015_04
Patent number
US09006275B2

Reaction notes

Loading…