Ethylmorpholine → 2-(S)-[2-(S)-Allyloxycarbonylamino-3-(4-carbamimidoyl-phenyl)-propionylamino]-pentanedioic acid 5-tert-butyl ester 1-methyl ester hydrochloride

HRID 1595141Notes

Reaction equation

HRID 1595141 reaction equation
[ClH:1].[CH2:2]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[NH:22])[NH2:21])=[CH:16][CH:15]=1)[C:10]([OH:12])=O)=[O:7])[CH:3]=[CH2:4].Cl.[CH3:24][O:25][C:26](=[O:38])[C@@H:27]([NH2:37])[CH2:28][CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31].[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.C(N1CCOCC1)C>CN(C=O)C>[ClH:1].[CH3:24][O:25][C:26](=[O:38])[C@@H:27]([NH:37][C:10](=[O:12])[C@@H:9]([NH:8][C:6]([O:5][CH2:2][CH:3]=[CH2:4])=[O:7])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[NH:22])[NH2:21])=[CH:16][CH:15]=1)[CH2:28][CH2:29][C:30]([O:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:31]

Participants

6

Reactant 4

HCID 7525EthylmorpholineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 16218751L-Glutamic acid, 5-(1,1-dimethylethyl) 1-methyl ester, hydrochloride (1:1)HCID 68613816(S)-2-Allyloxycarbonylamino-3-(4-carbamimidoylphenyl)propionic Acid Hydrochloride

Product 1

HCID 686148872-(S)-[2-(S)-Allyloxycarbonylamino-3-(4-carbamimidoyl-phenyl)-propionylamino]-pentanedioic acid 5-tert-butyl ester 1-methyl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2-(S)allyloxycarbonylamino-3-(4-carbamimidoyl-phenyl)-propionic acid hydrochloride (3.48 g, 10.6 mmol) and 2-(S)-amino-pentanedioic acid 5-tert-butyl ester 1-methyl ester hydrochloride (2.7 g, 10.6 mmol) in 20 ml of DMF were added at −15° C. TOTU (3.83 g, 11.67 mmol) and N-ethylmorpholine (2.7 ml, 21.2 mmol). The mixture was stirred for 1 hour and then allowed to warm to room temperature. After evaporation, ethyl acetate was added to the residue and the organic layer was extracted with aqueous sodium hydrogen carbonate solution, potassium hydrogen sulfate solution, and water. The organic layer was evaporated. Yield: 2.8 g (50%). MS: m/z=491.3 (M+H)+.

Workup

  1. customAfter evaporation, ethyl acetate
  2. additionwas added to the residue
  3. extractionthe organic layer was extracted with aqueous sodium hydrogen carbonate solution, potassium hydrogen sulfate solution, and water
  4. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-645ee4743164483b94b7cfd67ecc2d21
Source dataset
uspto-grants-2001_09
Patent number
US06287794B1

Reaction notes

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