1-Hydroxybenzotriazole → HCID 131717640, compound

HRID 373393Notes

Reaction equation

HRID 373393 reaction equation
[C:1]([O:5][C:6](=[O:21])[C@H:7]([C@@H:16]([NH2:20])[CH:17]([CH3:19])[CH3:18])[NH:8][C:9](=[O:15])[CH:10]([OH:14])[CH2:11][CH2:12][CH3:13])([CH3:4])([CH3:3])[CH3:2].[C:22]([NH:29][C@H:30]([C:34](O)=[O:35])[CH:31]([CH3:33])[CH3:32])([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[C:1]([O:5][C:6](=[O:21])[CH:7]([CH:16]([NH2:20])[CH:17]([CH3:18])[CH3:19])[N:8]([C:34](=[O:35])[C@H:30]([CH:31]([CH3:32])[CH3:33])[NH:29][C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[C:9](=[O:15])[CH:10]([OH:14])[CH2:11][CH2:12][CH3:13])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 83693Boc-L-ValineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86746328HCID 86746328, compound

Product 1

HCID 131717640HCID 131717640, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The ester compound thus formed was admixed with 155.9 mg (0.718 mmol) of Boc-L-valine, 176.1 mg (1.303 mmol) of N-hydroxyl-benzotriazole and 3.5 ml of dichloromethane. The resulting reaction mixture was cooled with ice, admixed with 499.4 mg (2.605 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, stirred for 2 hours, and further stirred at room temperature for 16.5 hours. The reaction mixture was diluted with 7 ml of dichloromethane, successively washed with 6 ml of a 1% aqueous citric acid solution, 6 ml of water, 6 ml of a saturated aqueous sodium hydrogen carbonate solution and 6 ml of water, dried over anhydrous sodium sulfate, and distilled to remove the solvent therefrom so that crude Boc-L-valyl-(2RS, 3RS)-3-amino-2 hydroxypentanoyl-D-leucine t-butyl ester was obtained as an amorphous material. The crude product was used in the next reaction step without a purification operation.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas cooled with ice
  3. stirringfurther stirred at room temperature for 16.5 hours
  4. washsuccessively washed with 6 ml of a 1% aqueous citric acid solution, 6 ml of water, 6 ml of a saturated aqueous sodium hydrogen carbonate solution and 6 ml of water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationdistilled
  7. customto remove the solvent

Sources & evidence

ORD record
ord-ff35b275843c4b7986d11ec63b17622c
Source dataset
uspto-grants-1992_11
Patent number
US05162500

Reaction notes

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