Beta-Alanine → HCID 14557735, compound

HRID 2165302Notes

Reaction equation

HRID 2165302 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].[CH2:7]([O:9][C:10]([C@@H:12]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:13][C@H:14]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:15](O)=[O:16])=[O:11])[CH3:8].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>C(Cl)Cl.C(OCC)C>[CH2:7]([O:9][C:10]([C@@H:12]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:13][C@H:14]([CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:15]([NH:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5])=[O:16])=[O:11])[CH3:8]

Participants

7

Reactant 4

HCID 239Beta-AlanineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 14557730HCID 14557730, compound

Product 1

HCID 14557735HCID 14557735, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.01 mole of 3-aminopropionic acid and 0.01 mole of (R*,R*)-4-ethoxycarbonyl-2,4-dibenzylbutyric acid in 40 ml of methylene chloride are added 0.01 mole of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 0.01 mole of triethylamine. The reaction mixture is stirred at room temperature for 3 days. Diethyl ether (250 ml) is added and the mixture is washed with 25 ml of water, 25 ml of 2N aqueous hydrochloric acid and 25 ml of saturated aqueous sodium bicarbonate solution. The organic layer is dried over magnesium sulfate and evaporated to give N-[4-ethoxycarbonyl-(R*,R*)-2,4-dibenzylbutyryl]-3-aminopropionic acid, the compound of example 5(a).

Workup

  1. washthe mixture is washed with 25 ml of water, 25 ml of 2N aqueous hydrochloric acid and 25 ml of saturated aqueous sodium bicarbonate solution
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-0d14597197cb4694b46feeceb6bee7ff
Source dataset
uspto-grants-1990_07
Patent number
US04939261

Reaction notes

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