1-Adamantanecarboxylic acid → HCID 178522740, compound

HRID 255112Notes

Reaction equation

HRID 255112 reaction equation
[N:1]1([CH2:7][CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[S:11][C:10]2=[NH:18])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:19]12([C:29](O)=[O:30])[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:27][CH:21]([CH2:22]3)[CH2:20]1)[CH2:26]2>>[N:1]1([CH2:7][CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[S:11]/[C:10]/2=[N:18]\[C:29]([C:19]23[CH2:28][CH:23]4[CH2:22][CH:21]([CH2:27][CH:25]([CH2:24]4)[CH2:26]2)[CH2:20]3)=[O:30])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 132351-Adamantanecarboxylic acidHCID 66858783HCID 66858783, compound

Product 1

HCID 178522740HCID 178522740, compoundYield 25.4%

Procedure

The product of Example 108A (0.20 g, 0.76 mmol) and adamantane-1-carboxylic acid (0.15 g, 0.84 mmol) were processed according to the method of Example 77B. Purification by column chromatography (SiO2, 0-30% methanol/methylene gradient) afforded 82 mg (25%) of the title compound. 1H NMR (CDCl3, 300 MHz) δ ppm 1.67-1.82 (m, 6 H), 1.99 (d, J=2.7 Hz, 6 H), 2.06 (s, 3 H), 2.62 (s, 4 H), 2.78 (s, 2 H), 3.70 (s, 4 H), 4.53 (s, 2 H), 7.22-7.37 (m, 2 H), 7.43 (t, J=7.6 Hz, 1 H), 7.65 (d, J=7.8 Hz, 1 H); MS (DCI/NH3) m/z 426 (M+H)+. Anal. Calculated for C24H31N3O2S.0.2H2O: C, 67.16; H, 7.37; N, 9.79. Found: C, 66.92; H, 7.59; N, 9.83.

Workup

  1. customPurification by column chromatography (SiO2, 0-30% methanol/methylene gradient)

Sources & evidence

ORD record
ord-f90951e1c69747b59052ddf54edc305a
Source dataset
uspto-grants-2011_01
Patent number
US07875639B2

Reaction notes

Loading…