1-Adamantanecarboxylic acid → HCID 24888214, compound

HRID 255090Notes

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

Participants

Reactant 2

HCID 132351-Adamantanecarboxylic acid

HCID 131728627HCID 131728627, compound

Product 1

HCID 24888214HCID 24888214, compoundYield 63%

Procedure

Adamantane-1-carboxylic acid (2.2 g, 12 mmol) and the product of Example 82A (2.9 g, 10 mmol) were processed according to the method of Example 77B Purification by column chromatography (SiO2, 20-35% ethyl acetate/hexanes gradient) afforded 0.25 g (63%) of the title compound. 1H NMR (CDCl3, 300 MHz) δ ppm 1.47 (s, 9 H), 1.71-1.75 (m, 6 H), 1.96-2.00 (m, 6 H), 2.00-2.04 (m, 3 H), 2.14 (s, 3 H), 2.21 (s, 3 H), 4.85-5.02 (m, 2 H); MS (DCI/NH3) m/z 405 (M+H)+. Anal. Calculated for C22H32N2O3S: C, 65.31; H, 7.97; N, 6.92 Found: C, 65.38; H, 7.95; N, 6.84.

Sources & evidence

ORD record: ord-6607a805a0564d9985fed0c0c6274691
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07875639B2

Reaction notes

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