4-Methylmorpholine → HCID 86749646, compound

HRID 1781127Notes

Reaction equation

HRID 1781127 reaction equation
Cl.[NH2:2][N:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:18])[CH2:13][CH2:14][C:15]([OH:17])=O)=[CH:7][CH:6]=1.CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:34][C@H:35]([C:42]#[CH:43])[CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38].C(N(C(C)C)CC)(C)C.CN(C1C=CC=CN=1)C>CN(C=O)C>[NH2:2][N:3]=[CH:4][C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12](=[O:18])[CH2:13][CH2:14][C:15]([NH:34][C@H:35]([C:42]#[CH:43])[CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])=[O:17])=[CH:9][CH:10]=1

Participants

8

Reactant 6

HCID 79724-MethylmorpholineHCID 218852-DimethylaminopyridineHCID 62365Isobutyl chloroformateHCID 81531DiisopropylethylamineHCID 10419270(S)-ethyl 3-amino-4-pentynoateHCID 699519434-[(4-(Aminoiminomethyl)phenyl)amino]-4-oxobutanoic acid hydrochloride

Product 1

HCID 86749646HCID 86749646, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[[4-(Aminoiminomethyl)phenyl]amino]-4-oxobutanoic acid hydrochloride was added to dry DMF (35 ml) followed by N-methylmorpholine (0.39 g, 1 eq.) and isobutyl chloroformate (0.53 g, 3.9 mmol) at 25° C. The mixture was stirred for 5 min. (S)-ethyl 3-amino-4-pentynoate was added followed by diisopropylethylamine and a catalytic amount of dimethylaminopyridine. After 1 hour, the solvent was removed under reduced pressure and the product was purified by reverse phase chromatography to give (3S)-ethyl 3-[[4-[[4-(aminoiminomethyl)phenyl]amino]-1,4-dioxobutyl]amino]-4-pentynoate.

Workup

  1. additionwas added
  2. customthe solvent was removed under reduced pressure
  3. customthe product was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-5a6738c6e3e64ced845e39bbb9e836f6
Source dataset
uspto-grants-1997_05
Patent number
US05631399

Reaction notes

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