Hydrochloric Acid → 2-Propylaminoacetic acid N-(1-adamantyl)amide

HRID 11443Notes

Reaction equation

HRID 11443 reaction equation
Cl.C(OCC)(=O)C.[C:8]12([NH:18][C:19](=[O:32])[CH2:20][N:21](C(OC(C)(C)C)=O)[CH2:22][CH2:23][CH3:24])[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2>>[C:8]12([NH:18][C:19](=[O:32])[CH2:20][NH:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH:12]3[CH2:11][CH:10]([CH2:16][CH:14]([CH2:13]3)[CH2:15]1)[CH2:9]2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 121366302-[N'(t-butoxycarbonyl)-N-propylamino]acetic acid N-(1-adamantyl)amide

Product 1

HCID 28703372-Propylaminoacetic acid N-(1-adamantyl)amideYield 108.9%

Procedure

Next, a 4 N solution of hydrogen chloride in ethyl acetate (55 ml, 0.22 mol) was added to 2-[N′(t-butoxycarbonyl)-N-propylamino]acetic acid N-(1-adamantyl)amide (7.68 g, 21.9 mmol), and the mixture was stirred at room temperature for one hour. The resulting crystals were filtered off with ethyl acetate and washed with ethyl acetate to give 5.97 g (95%) of the titled compound as colorless crystals.

Workup

  1. filtrationThe resulting crystals were filtered off with ethyl acetate
  2. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-11ce434220d74253ad122a096065b5d9
Source dataset
uspto-grants-2006_08
Patent number
US07098226B2

Reaction notes

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