1-Adamantanecarboxylic acid → HCID 24888214, compound

HRID 1469974Notes

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, 9H), 1.71-1.75 (m, 6H), 1.96-2.00 (m, 6H), 2.00-2.04 (m, 3H), 2.14 (s, 3H), 2.21 (s, 3H), 4.85-5.02 (m, 2H); 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.

Workup

customPurification by column chromatography (SiO2, 20-35% ethyl acetate/hexanes gradient)

Sources & evidence

ORD record: ord-51e596a213344606a876d806b900ae6d
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006275B2

Reaction notes

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