1-Adamantanecarboxylic acid → HCID 66859715, compound

HRID 1469947Notes

Reaction equation

HRID 1469947 reaction equation
[CH3:1][C:2]1[N:3]([CH2:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[C:4](=[NH:8])[S:5][C:6]=1[CH3:7].[C:16]12([C:26](O)=[O:27])[CH2:25][CH:20]3[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]3)[CH2:17]1)[CH2:23]2>>[CH3:1][C:2]1[N:3]([CH2:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[C:4](=[N:8][C:26]([C:16]23[CH2:25][CH:20]4[CH2:19][CH:18]([CH2:24][CH:22]([CH2:21]4)[CH2:23]2)[CH2:17]3)=[O:27])[S:5][C:6]=1[CH3:7]

Participants

3

Reactant 2

HCID 132351-Adamantanecarboxylic acidHCID 66860587HCID 66860587, compound

Product 1

HCID 66859715HCID 66859715, compoundYield 13.1%

Procedure

The product of Example 58A (0.11 g, 0.49 mmol) and adamantane-1-carboxylic acid (97 mg, 0.54 mmol) were processed as described in Example 3B. Purification by column chromatography (SiO2, 0-20% methanol/methylene chloride gradient) afforded 25 mg (13%) of the title compound. MS (DCI/NH3) m/z 389 (M+H)+. Anal. Calculated for C22H32N2O2S: C, 68.00; H, 8.30; N, 7.21. Found: C, 67.61; H, 8.67; N, 7.17.

Workup

  1. customPurification by column chromatography (SiO2, 0-20% methanol/methylene chloride gradient)

Sources & evidence

ORD record
ord-4078728c354b43cba3a1eae73ae18328
Source dataset
uspto-grants-2015_04
Patent number
US09006275B2

Reaction notes

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