Ammonia → 4-Aminotricyclo[3.3.1.13,7]decane-2-carboxylic acid
Reaction equation
O=[C:2]1[CH:9]2[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:11][CH:3]1[CH:4]3[C:12]([OH:14])=[O:13])[CH2:8]2.[NH3:15]>C(O)C.[Pt]=O>[NH2:15][CH:2]1[CH:9]2[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:11][CH:3]1[CH:4]3[C:12]([OH:14])=[O:13])[CH2:8]2Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
4.7 Grams of 4-oxo-2-adamantanecarboxylic acid [preparation is described in G. Snatzke, et. al., CHEM. BER. 100:1710-1724(1967)] is hydrogenated in 75 ml of ethanol over 0.47 g of platinum oxide in the presence of ammonia gas under 60 psi of pressure at room temperature. The solvent is removed under reduced pressure and 15 ml of water is added and removed under reduced pressure. Another 15 ml of water is added and removed under reduced pressure then the residue is dried at 100° C. in a vacuum oven for 1 hour to give 4-amino-2-adamantanecarboxylic acid which is represented by the following formula ##STR63## Substitution of an equivalent quantity of 4-amino-2-adamantanecarboxylic acid for the 3-amino-1-adamantanecarboxylic acid of Example 1 and substantial repetition of the procedures detailed in Examples 1 through 9 provides methyl L-tyrosyl-D-methionyl-glycyl-L-phenylalanyl-4-amino-2-adamantanecarboxylate hydrochloride which is represented by the following formula ##STR64##
Workup
- customThe solvent is removed under reduced pressure and 15 ml of water
- additionis added
- customremoved under reduced pressure
- additionAnother 15 ml of water is added
- customremoved under reduced pressure
- customthe residue is dried at 100° C. in a vacuum oven for 1 hour
Sources & evidence
- ORD record
- ord-afbbdeedfb334313bf73730dcfbbe51f
- Source dataset
- uspto-grants-1981_06
- Patent number
- US04273704
Reaction notes
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