Diisopropylethylamine → HCID 178456502, compound

HRID 248091Notes

Reaction equation

HRID 248091 reaction equation
[CH2:1]([N:4]1[C:12](=[O:13])[C:11]2[N:10]=[C:9]([CH:14]([CH3:27])[CH2:15][C:16]3[CH:26]=[CH:25][C:19]([O:20][CH2:21][C:22](O)=[O:23])=[CH:18][CH:17]=3)[NH:8][C:7]=2[N:6]([CH2:28][CH2:29][CH3:30])[C:5]1=[O:31])[CH2:2][CH3:3].Cl.[C:33]([O:37][C:38](=[O:42])[C@H:39]([CH3:41])[NH2:40])([CH3:36])([CH3:35])[CH3:34].OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC.C(N(C(C)C)CC)(C)C>C(Cl)Cl.C(OCC)(=O)C>[CH2:1]([N:4]1[C:12](=[O:13])[C:11]2[N:10]=[C:9]([CH:14]([CH3:27])[CH2:15][C:16]3[CH:26]=[CH:25][C:19]([O:20][CH2:21][C:22]([NH:40][C@H:39]([C:38]([O:37][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:42])[CH3:41])=[O:23])=[CH:18][CH:17]=3)[NH:8][C:7]=2[N:6]([CH2:28][CH2:29][CH3:30])[C:5]1=[O:31])[CH2:2][CH3:3]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11275390tert-Butyl alaninate hydrochlorideHCID 178418300HCID 178418300, compoundHCID 178456503HCID 178456503, compound

Product 1

HCID 178456502HCID 178456502, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Mix (-)-2-[4-[2-(2,3,6,9-tetrahydro-1,3-dipropyl-2,6-dioxo-1H-purin-8-yl)propyl]phenoxy]acetic acid (4.28 g, 10 mmol), L-alanine t-butylester hydrochloride (965 mg, 5.3 mmol), hydroxybenztriazole (1.65 g, 11 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.1 g, 11 mmol). Add a solution of diisopropylethylamine (3.8 mL) in methylene chloride (20 mL) and stir at room temperature for several hours. Dilute with ethyl acetate (150 mL), wash with cold 0.5N hydrochloric acid, saturated aqueous sodium hydrogen carbonate and brine. Dry (MgSO4) and evaporate the solvent in vacuo to give the title compound.

Workup

  1. washwash with cold 0.5N hydrochloric acid, saturated aqueous sodium hydrogen carbonate and brine
  2. dry with materialDry (MgSO4)
  3. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-1e9c22faa95147a69aa72570853a35a8
Source dataset
uspto-grants-1993_05
Patent number
US05208240

Reaction notes

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