1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)- → HCID 67890866, compound

HRID 1189920Notes

Reaction equation

HRID 1189920 reaction equation
CCN=C=NCCCN(C)C.Cl.[N:13]1([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19][CH2:18][C@H:14]1[C:15]([OH:17])=O.[NH:28]1[CH2:41][CH2:40][CH2:39][C@H:29]1[C:30]([NH:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:31]>C1COCC1>[N:13]1([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19][CH2:18][C@H:14]1[C:15]([N:28]1[CH2:41][CH2:40][CH2:39][C@H:29]1[C:30]([NH:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:31])=[O:17]

Participants

5

Reactant 3

HCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6552381L-Prolinanilide

Product 1

HCID 67890866HCID 67890866, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

201 mg (1.05 mmol) of EDCl was added to 5 ml of THF solution of 100 mg (0.526 mmol) of Boc-Pro-OH (manufactured by Tokyo Chemical Industry Co., Ltd), and 113 mg (0.526 mmol) of H-Pro-NHPh (manufactured by Tokyo Chemical Industry Co., Ltd), followed by stirring for 6 hours at room temperature. After a reaction mixture was concentrated under reduced pressure, the concentrate was extracted by adding water and ethyl acetate. After an organic layer was washed sequentially with a diluted hydrochloric acid, an aqueous solution of sodium hydrogen carbonate and water (one time for each), it was concentrated under reduced pressure, thereby obtaining crude amide. The obtained amide compound was purified by a silica gel column chromatography (hexane/ethyl acetate=5/1 to 1/1 (volume ratio)), thereby obtaining 150 mg of the product with a yield of 73.6%.

Workup

  1. concentrationAfter a reaction mixture was concentrated under reduced pressure
  2. extractionthe concentrate was extracted
  3. additionby adding water and ethyl acetate
  4. washAfter an organic layer was washed sequentially with a diluted hydrochloric acid
  5. concentrationan aqueous solution of sodium hydrogen carbonate and water (one time for each), it was concentrated under reduced pressure
  6. customobtaining crude amide
  7. customThe obtained amide compound was purified by a silica gel column chromatography (hexane/ethyl acetate=5/1 to 1/1 (volume ratio))

Sources & evidence

ORD record
ord-7a23178b3e51455a863e47779b675293
Source dataset
uspto-grants-2014_03
Patent number
US08674144B2

Reaction notes

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