Triethylamine → 3-(3-(S)-Amino-2-oxopyrrolidin-1-ylmethyl)benzonitrile hydrochloride

HRID 619782

Reaction equation

HRID 619782 reaction equation
C([C@@H:8]([CH3:15])[C:9]([NH2:14])(N)[C:10]([OH:12])=O)(OC(C)(C)C)=O.C([N:18]([CH2:21][CH3:22])CC)C.OC1[C:32]2[N:31]=NN[C:28]=2[CH:27]=[CH:26][CH:25]=1.[ClH:33].[CH3:34]N(C)CCCN=C=NCC>C1COCC1>[ClH:33].[NH2:14][C@H:9]1[CH2:8][CH2:15][N:31]([CH2:32][C:28]2[CH:34]=[C:22]([CH:25]=[CH:26][CH:27]=2)[C:21]#[N:18])[C:10]1=[O:12]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86752309(S)-Boc-Diaminobutyric acidHCID 178418300HCID 178418300, compound

Product 1

HCID 228707863-(3-(S)-Amino-2-oxopyrrolidin-1-ylmethyl)benzonitrile hydrochlorideYield 85.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (S)-Boc-diaminobutyric acid (25 g, 115 mmol), triethylamine (35 g, 344 mmol), and hydroxybenzotriazole (19.3 g, 143 mmol) in 0.5 L of THF is added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (27.4 g, 143 mmol). The solution is heated to 60° C. over 15 minutes. A white precipitate forms and the solution is kept at 60° C. for 4 hours. After this time, the solution is filtered and the collected liquid is concentrated. The crude product is purified by column chromatography in a gradient of 1% MeOH/CH2Cl2 to 3% MeOH/CH2Cl2 to afford the title compound (19.6 g, 98 mmol) as a white solid.

Workup

  1. filtrationAfter this time, the solution is filtered
  2. concentrationthe collected liquid is concentrated
  3. customThe crude product is purified by column chromatography in a gradient of 1% MeOH/CH2Cl2 to 3% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-b3888683d46e4beab8287223173bb7f2
Source dataset
uspto-grants-1999_09
Patent number
US05958918

Linked notes

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