Triethylamine → HCID 86664667, compound

HRID 1046983Notes

Reaction equation

HRID 1046983 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN([C:25]([O:29][N:30]1N=NC2C=CC=C[C:31]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.Cl.CNOC>CN(C)C=O>[CH3:25][O:29][N:30]([CH3:31])[C:17]([C:16]1[CH:20]=[CH:21][C:13]([C:9]2([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:12][CH2:11][CH2:10]2)=[CH:14][CH:15]=1)=[O:19]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 583451244-{1-[(tert-Butoxycarbonyl)amino]cyclobutyl}benzoic acid

Product 1

HCID 86664667HCID 86664667, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(1-((tert-butoxycarbonyl)amino)cyclobutyl)benzoic acid (2.5 g, 1 eq.) in dimethylformamide (10 mL) was added HBTU (3.41 g, 1.05 eq.) followed by triethylamine (6 mL, 5 eq.). The reaction mixture was stirred at room temperature for 10 minutes then the N,O-dimethylhydroxylamine hydrochloride was added (4.3 g, 5 eq.) and the mixture was stirred for 3 days. The reaction mixture was poured onto water (50 mL) and extracted with ethyl acetate (3×100 mL). The combined extracts were washed with water (100 mL), brine (100 mL) then dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography (20-50% ethyl acetate in dichloromethane), giving tert-butyl (1-(4-(methoxy(methyl)carbamoyl)phenyl)cyclobutyl)carbamate (1.5 g, 52%). LCMS: 335 [M+H].

Workup

  1. stirringthe mixture was stirred for 3 days
  2. additionThe reaction mixture was poured onto water (50 mL)
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. washThe combined extracts were washed with water (100 mL), brine (100 mL)
  5. dry with materialthen dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was purified by column chromatography (20-50% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-67bb87a8c5a64958a4f074947a180519
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

Loading…