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

HRID 2075879Notes

Reaction equation

HRID 2075879 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-7d8297c6213a4c86abf8651aad0f3ca2
Source dataset
uspto-grants-2011_04
Patent number
US07923461B2

Reaction notes

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