1-Hydroxybenzotriazole → HCID 86752374, compound

HRID 1598453Notes

Reaction equation

HRID 1598453 reaction equation
[CH2:1]([C@@H:5]1[NH:10][CH2:9][CH2:8][N:7]([C:11](=[O:20])[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:13]=2[CH3:19])[CH2:6]1)[CH2:2][CH2:3][CH3:4].[C:21]([O:25][C:26]([NH:28][C@H:29]([CH2:33][C:34]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:30](O)=[S:31])=[O:27])([CH3:24])([CH3:23])[CH3:22].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C)C=O>[C:21]([O:25][C:26]([NH:28][C@H:29]([CH2:33][C:34]([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[C:30]([N:10]1[CH2:9][CH2:8][N:7]([C:11](=[O:20])[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:13]=2[CH3:19])[CH2:6][C@@H:5]1[CH2:1][CH2:2][CH2:3][CH3:4])=[S:31])=[O:27])([CH3:24])([CH3:22])[CH3:23]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67629599HCID 67629599, compoundHCID 178454172HCID 178454172, compound

Product 1

HCID 86752374HCID 86752374, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3(S)-n-Butyl-1-(2,3-dimethylbenzoyl)piperazine (0.240 g, 0.874 mmol) and 2(R)-tert-butoxycarbonylamino-3-triphenylmethylthiopropionic acid (0.405 g, 0.874 mmol) were dissolved in dimethylformamide. To this solution was added HOBT (0.114 g, 0.874 mmol), and EDC.HCl (0.184 g, 0.962 mmol). The reaction was stirred under nitrogen overnight. The dimethylformamide was removed in vacuo and the residue partitioned between ethyl acetate and water. The organic phase was washed with several portions of water, saturated sodium chloride solution, and dried over magnesium sulfate. Filtration and evaporation of solvent gave the crude product, which was chromatographed on silica gel with 50% ethyl acetate in hexane. The title compound as a white foam (0.620 g).

Workup

  1. customThe dimethylformamide was removed in vacuo
  2. customthe residue partitioned between ethyl acetate and water
  3. washThe organic phase was washed with several portions of water, saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration and evaporation of solvent

Sources & evidence

ORD record
ord-f97c1d51bf084037a89ccebdc6c326ae
Source dataset
uspto-grants-1998_04
Patent number
US05736539

Reaction notes

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