1-Hydroxybenzotriazole → HCID 491693, compound

HRID 1489765Notes

Reaction equation

HRID 1489765 reaction equation
[C:1]([NH:13][C@H:14]([C:18]([OH:20])=O)[CH:15]([CH3:17])[CH3:16])(=[O:12])[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH:21]([N:24]([CH2:33][C@@H:34]([OH:44])[C@@H:35]([NH2:43])[CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])([CH3:23])[CH3:22].ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.CI>CN(C=O)C.C(OCC)(=O)C>[CH:21]([N:24]([CH2:33][C@@H:34]([OH:44])[C@@H:35]([NH:43][C:18](=[O:20])[C@H:14]([CH:15]([CH3:16])[CH3:17])[NH:13][C:1](=[O:12])[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)[CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:30])[CH3:31])=[O:27])([CH3:23])[CH3:22]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 10236463N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide methyliodideHCID 10707328HCID 10707328, compoundHCID 67551723HCID 67551723, compound

Product 1

HCID 491693HCID 491693, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 0.0643 g (0.24 mmol) of the acid from Step A, 0.0797 g (0.236 mmol) of the the amine from Step B, 0.032 g (0.24 mmol) of 1-hydroxybenzotriazole in 0.5 ml of anhydrous DMF was added 0.071 g (0.24 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide methiodide. After stirring overnight at room temperature the mixture was diluted to 30 ml with ethyl acetate and Washed successively with water, 5% aqueous sodium bicarbonate, 2% aqueous potassium bisulfate solution, and saturated sodium chloride solution and dried over anhydrous magnesium sulfate. Evaporation of the solvent under reduced pressure and purification of the residue by column chromatography (silica gel, hexane/ethyl acetate 3:2) gave 0.091 g (65% yield) of the title compound, melting at 186°-189° C.: Rf (B)=0.19; Rf (C)=0.83; NMR (CDCl3) 1.0 (m, 12H, val and isopropyl CH3); 1.71 (s, 9H, t-butyl CH3); 2.3 (m, 1 H, val CH-β); 2.5-3.27 (m, 3H, butyl CH-3, CH2); 3.5 (m, 1 H, isopropyl CH); 4.31 (m, 2H, val CH-α, OH); 5.43 (broad s, 1 H, carbazate NH); 6.22 (broad d, 1H, butyl NH); 6.7-8.73 (m, 12H, aromatic, NH).

Workup

  1. washWashed successively with water, 5% aqueous sodium bicarbonate, 2% aqueous potassium bisulfate solution, and saturated sodium chloride solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customEvaporation of the solvent
  4. customunder reduced pressure and purification of the residue by column chromatography (silica gel, hexane/ethyl acetate 3:2)

Sources & evidence

ORD record
ord-224a4785269a4bccbc08c2d1c4d31e0e
Source dataset
uspto-grants-1997_10
Patent number
US05679688

Reaction notes

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