Diisopropylethylamine → HCID 49835495, compound

HRID 1752316Notes

Reaction equation

HRID 1752316 reaction equation
[C:1]1([CH3:17])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1([CH2:13][C:14]([OH:16])=[O:15])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.Cl[C:19]([O:21][CH:22]1[CH:29]2[CH2:30][CH:25]3[CH2:26][CH:27]([CH2:31][CH:23]1[CH2:24]3)[CH2:28]2)=[O:20].CCN(C(C)C)C(C)C>C(#N)C>[CH:29]12[CH2:30][CH:25]3[CH2:26][CH:27]([CH2:31][CH:23]([CH2:24]3)[CH:22]1[O:21][C:19]([N:10]1[CH2:9][CH2:8][C:7]([CH2:13][C:14]([OH:16])=[O:15])([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=3[CH3:17])[CH2:12][CH2:11]1)=[O:20])[CH2:28]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 108785372-adamantyl ChloroformateHCID 58171614HCID 58171614, compound

Product 1

HCID 49835495HCID 49835495, compoundYield 16.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A fraction of the above aqueous solution (contains ˜15 mg of 2-(4-o-tolylpiperidin-4-yl)acetic acid, 0.064 mmol) was mixed with 2-adamantyl chloroformate (15 mg, 1.1 equiv). i-Pr2NEt (100 μL, excess) was added. Acetonitrile was added to make the mixture homogeneous. After stirring for 1 h at rt, the mixture was acidified and purified by prep HPLC to afford 2-(1-(2-adamantyloxycarbonyl)-4-o-tolylpiperidin-4-yl)acetic acid (4.4 mg). LC-MS Method 1 tR=2.13 min, m/z=412, 1H NMR (CDCl3) [selected resonances] 7.14 (m, 4H), 4.82 (s, 1H), 3.72 (br s, 2H), 2.78 (s, 2H), 2.52 (s, 3H), 2.46 (dt, 2H), 2.0 (m, 5H), 1.06 (d, 3H).

Workup

  1. custompurified by prep HPLC

Sources & evidence

ORD record
ord-0d62f0e486464024afd42bc22fe4954f
Source dataset
uspto-grants-2015_10
Patent number
US09163012B2

Reaction notes

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