Pyrrolidone carboxylic acid → HCID 66750924, compound

HRID 534923Notes

Reaction equation

HRID 534923 reaction equation
Cl.Cl.[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)([CH3:6])([CH3:5])[CH3:4].[NH:19]1[C:23](=[O:24])[CH2:22][CH2:21][CH:20]1[C:25](O)=[O:26].C(N(CC)CC)C.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(#N)C>[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][N:16]([C:25]([CH:20]2[NH:19][C:23](=[O:24])[CH2:22][CH2:21]2)=[O:26])[CH2:15][CH2:14]1)([CH3:6])([CH3:4])[CH3:5]

Participants

7

Reactant 5

HCID 499Pyrrolidone carboxylic acidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 667511491-(2-Tert-butylphenyl)piperazine dihydrochloride

Product 1

HCID 66750924HCID 66750924, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(2-tert-butylphenyl)piperazine dihydrochloride obtained in Reference Example 1 (1.00 g, 3.43 mmol), DL-pyroglutamic acid (0.49 g, 3.78 mmol), triethylamine (0.73 g, 7.20 mmol), EDCI (0.72 g, 3.78 mmol) and HOBt (0.58 g, 3.78 mmol) in acetonitrile (30 mL) was stirred at room temperature for 16 h. The reaction mixture was concentrated under reduced pressure and the resulting residue was partitioned between ethyl acetate and 10% sodium hydrogen carbonate solution. The resulting white precipitate was collected by filtration and washed with diethyl ether to afford the title compound (1.03 g, 91%) as a off-white solid, mp 290° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was partitioned between ethyl acetate and 10% sodium hydrogen carbonate solution
  3. filtrationThe resulting white precipitate was collected by filtration
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-2120162b9e27449d92fbf3325c20d80c
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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