Hydrochloric Acid → methyl L-phenylalanyl-3-amino-1-adamantanecarboxylate hydrochloride

HRID 1680571

Reaction equation

HRID 1680571 reaction equation
C([NH:8][C@H:9]([C:17]([CH:19]1[C:26]2([NH2:28])[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:29][C:20]1([C:30]([O:32][CH3:33])=[O:31])[CH2:21]3)[CH2:25]2)=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(OC(C)(C)C)=O.[ClH:34]>O1CCOCC1>[ClH:34].[NH2:8][C@H:9]([C:17]([CH:19]1[C:26]2([NH2:28])[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:29][C:20]1([C:30]([O:32][CH3:33])=[O:31])[CH2:21]3)[CH2:25]2)=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 70566312methyl Boc-phenylalanyl-3-amino-1-adamantanecarboxylate

Product 1

HCID 70565564methyl L-phenylalanyl-3-amino-1-adamantanecarboxylate hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

5.48 g of methyl Boc-phenylalanyl-3-amino-1-adamantanecarboxylate is dissolved in 15 ml of dioxane and 20 ml of a 5.9 M solution of hydrogen chloride in dioxane is added. After standing for 10 minutes at room temperature the solvent is removed under reduced pressure and the residue is stirred with diethyl ether. The crystalline product is collected by filtration, washed with diethyl ether and dried in a vacuum oven for 16 hours at 50° C. and 0.1 mm pressure to give methyl L-phenylalanyl-3-amino-1-adamantanecarboxylate hydrochloride which is represented by the following formula ##STR24##

Workup

  1. customthe solvent is removed under reduced pressure
  2. filtrationThe crystalline product is collected by filtration
  3. washwashed with diethyl ether
  4. customdried in a vacuum oven for 16 hours at 50° C.

Sources & evidence

ORD record
ord-47a06edf424944b2b6762ac2279364ed
Source dataset
uspto-grants-1981_06
Patent number
US04273704

Linked notes

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