4-Methylmorpholine → HCID 178500446, compound

HRID 378133Notes

Reaction equation

HRID 378133 reaction equation
Cl.[NH:2]([C:6]1[CH:7]=[C:8]([CH:16]=[CH:17][CH:18]=1)[C:9](=[O:15])[NH:10][CH2:11][C:12]([OH:14])=O)[C:3]([NH2:5])=N.Cl.[NH2:20][CH:21]([CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH2:22][C:23]([O:25][CH3:26])=[O:24].C[N:33]1CCOCC1>CN(C=O)C.N1C=CC=CC=1.CN(C1C=CN=CC=1)C.O>[NH2:33][N:5]=[CH:3][NH:2][C:6]1[CH:7]=[C:8]([C:9]([NH:10][CH2:11][C:12]([NH:20][CH:21]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH2:27][C:28]([O:30][CH3:31])=[O:29])=[O:14])=[O:15])[CH:16]=[CH:17][CH:18]=1

Participants

8

Reactant 3

HCID 79724-MethylmorpholineHCID 12900041Dimethyl 3-aminopentanedioate hydrochlorideHCID 178479373HCID 178479373, compound

Product 1

HCID 178500446HCID 178500446, compound

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of m-guanidinohippuric acid HCl (1.5 g) in DMF (4.5 ml) and pyridine (4.5 ml) was treated with DSC (1.8 g) and a catalytic amount of DMAP. After 2 hours, a solution of dimethyl 3-aminoglutarate HCl (1.1 g) and NMM (350 μl) in H2O (3 ml) was added to the reaction. The reaction was stirred overnight at room temperature and the product was isolated by HPLC. 1.5 g of 3-[[2-[[[3-[(aminoiminomethyl)amino]phenyl]-carbonyl]amino]acetyl]amino]pentanedioic acid, bismethyl ester was obtained as a white solid. MS and 1H-NMR were consistent with the desired product.

Workup

  1. customthe product was isolated by HPLC

Sources & evidence

ORD record
ord-11019b59d21b4e8ebef44a255e03d216
Source dataset
uspto-grants-2000_02
Patent number
US06028223

Reaction notes

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