Dimethylformamide → HCID 53728725, compound

HRID 1374668Notes

Reaction equation

HRID 1374668 reaction equation
[C:1]([C@@H:4]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:5][S:6][S:7][CH2:8][C@@H:9]([C:18](O)=[O:19])[NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])([OH:3])=O.[CH3:29][O:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35][NH2:36])=[CH:33][CH:32]=1.ON1[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=2N=N1.CCN=C=NCCC[N:57]([CH3:59])C.Cl.CN([CH:64]=[O:65])C>C(Cl)Cl.C(Cl)(Cl)Cl>[CH3:29][O:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35][NH:36][C:1]([C@@H:4]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:5][S:6][S:7][CH2:8][C@@H:9]([C:18](=[O:19])[NH:57][CH2:59][C:43]2[CH:48]=[CH:47][C:46]([O:65][CH3:64])=[CH:45][CH:44]=2)[NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:15])[CH3:16])=[O:12])=[O:3])=[CH:33][CH:32]=1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 754524-MethoxybenzylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 1096116610389-65-8

Product 1

HCID 53728725HCID 53728725, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Bis((2R)-carboxy-2-t-butoxycarbonylaminoethyl)disulfide (5 g), 4-methoxybenzylamine (3.7 ml) and 1-hydroxybenzotriazole (3.84 g) were dissolved in a mixture of methylene chloride (50 ml) and DMF (10 ml). The solution was cooled with ice and EDC-HCl (5.45 g) was added thereto. The mixture was stirred for 12 hours. The reaction mixture was diluted with chloroform, washed with 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride, successively, dried over anhydrous magnesium sulfate. The organic layer was concentrated and the residue was washed with diehylether to give the title compound (8.15 g) having the following physical data.

Workup

  1. additionwas added
  2. washwashed with 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride
  3. dry with materialsuccessively, dried over anhydrous magnesium sulfate
  4. concentrationThe organic layer was concentrated
  5. washthe residue was washed with diehylether

Sources & evidence

ORD record
ord-eb4b9133a9a34468811a1972fdb194fe
Source dataset
uspto-grants-2007_01
Patent number
US07166590B2

Reaction notes

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