N-Benzylglycine ethyl ester → HCID 66593062, compound

HRID 1092301Notes

Reaction equation

HRID 1092301 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[N:11]=[C:12]=[O:13])[CH2:8]2.[CH2:14]([O:16][C:17](=[O:27])[CH2:18][NH:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:15]>CCOCC>[CH2:14]([O:16][C:17](=[O:27])[CH2:18][N:19]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:12]([NH:11][CH:2]1[CH:1]2[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]1[CH2:4]3)[CH2:8]2)=[O:13])[CH3:15]

Participants

4

Reactant 2

HCID 80908N-Benzylglycine ethyl esterHCID 128826302-Isocyanatoadamantane

Product 1

HCID 66593062HCID 66593062, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-Adamantyl-isocyanate (CAS 71189-14-5, made from 2-aminoadamantane according to Eur. J. Med. Chem. 28 (1), 1993, 37-45, 500 mg) and commercially available benzylamino-acetic acid ethyl ester (572 mg) were dissolved in absolute ether (25 mL) under argon and stirred at RT for 12 hours. A colorless precipitate was formed. The reaction mixture was concentrated in vacuo and the residue was triturated with hexanes (30 mL) for one hour. The suspension was filtered and the solid was dried in vacuo to give (3-adamantan-2-yl-1-benzyl-ureido)-acetic acid ethyl ester (823 mg). MS (ESI): 371.2 (MH+).

Workup

  1. customA colorless precipitate was formed
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was triturated with hexanes (30 mL) for one hour
  4. filtrationThe suspension was filtered
  5. customthe solid was dried in vacuo

Sources & evidence

ORD record
ord-d5e2538834b642d8a18b017d44c4ed56
Source dataset
uspto-grants-2012_03
Patent number
US08129423B2

Reaction notes

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