HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Triethylamine → (S)-3-phenethylcarbamoyl-tetrahydro-pyridazine-1-carboxylic acid benzyl ester

HRID 1668413
Notes
Print preview

Reaction equation

HRID 1668413 reaction equation
[CH2:1]([NH:9][C:10]([C@@H:12]1[CH2:17][CH2:16][CH2:15][NH:14][NH:13]1)=[O:11])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CCN(CC)CC.[CH2:25]([O:32][C:33](Cl)=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(Cl)Cl>[CH2:25]([O:32][C:33]([N:14]1[CH2:15][CH2:16][CH2:17][C@@H:12]([C:10](=[O:11])[NH:9][CH2:1][CH2:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:13]1)=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 57612768(S)-hexahydro pyridazine-3-carboxylic acid phenethyl-amide

Product 1

HCID 57612817(S)-3-phenethylcarbamoyl-tetrahydro-pyridazine-1-carboxylic acid benzyl esterYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent
2×

Conditions

Temperature
-5 °C

Procedure

To a solution of (S)-hexahydro pyridazine-3-carboxylic acid phenethyl-amide (376 mg, 1.59 mmol) and Et3N (0.66 mL) in CH2Cl2 (10 mL) at 0° C., is added benzylchloroformate (270 mg, 1.59 mmol) dropwise. After stirring at −5° C. for 1.5 hours, the reaction mixture is diluted with CH2Cl2 (50 mL) and washed with 10 mL of water. The organic layer is dried over Na2SO4 and concentrated to give (S)-3-phenethylcarbamoyl-tetrahydro-pyridazine-1-carboxylic acid benzyl ester (580 mg) as pale gum without further purification for next step reaction. (NMR and MS data confirmed, U-3133-59).

Workup

  1. washwashed with 10 mL of water
  2. dry with materialThe organic layer is dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-84db6e2e5d114ae698747ced9b59153a
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07989441B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes