L-Pyroglutamic Acid → HCID 20698877, compound
Reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([OH:9])=O.ON1C(=O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH3:34][O:35][C:36](=[O:58])[C@H:37]([CH2:54][CH2:55][S:56][CH3:57])[NH:38][C:39](=[O:53])[C:40]1[CH:45]=[CH:44][C:43]([NH2:46])=[CH:42][C:41]=1[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>CN(C=O)C.C(OCC)(=O)C>[CH3:34][O:35][C:36](=[O:58])[C@H:37]([CH2:54][CH2:55][S:56][CH3:57])[NH:38][C:39](=[O:53])[C:40]1[CH:45]=[CH:44][C:43]([NH:46][C:7]([CH:2]2[NH:1][C:5](=[O:6])[CH2:4][CH2:3]2)=[O:9])=[CH:42][C:41]=1[C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
To a solution of L-pyroglutamic acid (49 mg, 0.38 mmol) in 5 mL of DMF was added 3-hydroxy,1,2,3-benzotriazin-4(3H)-one (62 mg, 0.38 mmol), (3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (58 mg, 0.30 mmol) and [4-amino-2-phenylbenzoyl-L-methionine methyl ester (90 mg, 0.38 mmol), prepared as in Example 192B, and the reaction mixture was stirred at 25° C. for 12 hours. The reaction mixture was taken up in ethyl acetate and washed with 10 mL 1N HCl, 5 mL satd aqueous NaHCO3 and brine (3×10 mL). The organic layer was dried over Na2SO4, filtered and evaporated. Purification by radial chromatography (2-5% methanol-ethyl acetate gradient) to give [4-(2-pyrrolidinone-5-ylcarbonylamino)-2-phenylbenzoyl]methionine methyl ester (92 mg, 79%) as a white solid.
Workup
- washwashed with 10 mL 1N HCl, 5 mL
- dry with materialThe organic layer was dried over Na2SO4
- filtrationfiltered
- customevaporated
- customPurification by radial chromatography (2-5% methanol-ethyl acetate gradient)
Sources & evidence
- ORD record
- ord-86e730028bb3464b824f9ebfa6b1b1d7
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06310095B1
Reaction notes
Loading…