Triethylamine → HCID 178454120, compound

HRID 707231Notes

Reaction equation

HRID 707231 reaction equation
Cl.[Cl:2][C:3]1[C:8]([C:9]([CH3:14])([CH3:13])[C:10]([OH:12])=O)=[CH:7][CH:6]=[CH:5][N:4]=1.[C:15]([O:19][C:20](=[O:27])[NH:21][C@H:22]1[CH2:25][C@H:24]([NH2:26])[CH2:23]1)([CH3:18])([CH3:17])[CH3:16].C(N(CC)CC)C>ClCCl.O>[C:15]([O:19][C:20](=[O:27])[NH:21][C@H:22]1[CH2:25][C@H:24]([NH:26][C:10](=[O:12])[C:9]([C:8]2[C:3]([Cl:2])=[N:4][CH:5]=[CH:6][CH:7]=2)([CH3:14])[CH3:13])[CH2:23]1)([CH3:18])([CH3:16])[CH3:17]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 86694174HCID 86694174, compound2×HCID 178454111HCID 178454111, compound

Product 1

HCID 178454120HCID 178454120, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

2-(2-Chloropyridin-3-yl)-2-methylpropanoic acid hydrochloride (intermediate 25, 992 mg, 4.20 mmol), tert-butyl(trans-3-aminocyclobutyl)carbamate (939 mg, 5.04 mmol), hatu (2077 mg, 5.46 mmol) and triethylamine (2.4 ml, 16.81 mmol) were dissolved in dichloromethane (8.4 mL). The reaction mixture was stirred at room temperature for 21 hours then diluted with water and extracted with dichloromethane. The organic was washed with saturated ammonium chloride and dried over magnesium sulfate. Evaporation under reduced pressure and purification using silica chromatography (0% to 100% ethyl acetate in hexane gradient) gave tert-butyl(trans-3-(2-(2-chloropyridin-3-yl)-2-methylpropanamido)cyclobutyl)carbamate (1327 mg, 3.61 mmol, 86% yield) as white solid.

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic was washed with saturated ammonium chloride
  3. dry with materialdried over magnesium sulfate
  4. customEvaporation
  5. customunder reduced pressure and purification

Sources & evidence

ORD record
ord-33130e38549f447d9d93eaa5b4580931
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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