Pyrrolidine → HCID 24689350, compound

HRID 1192273Notes

Reaction equation

HRID 1192273 reaction equation
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1.C(N(C(C)C)CC)(C)C.[C:39]([O:43][C:44]([NH:46][CH2:47][CH2:48][C:49](O)=[O:50])=[O:45])([CH3:42])([CH3:41])[CH3:40]>ClCCl>[O:50]=[C:49]([N:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1)[CH2:48][CH2:47][NH:46][C:44](=[O:45])[O:43][C:39]([CH3:41])([CH3:40])[CH3:42]

Participants

6

Reactant 4

HCID 31268PyrrolidineHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 24689350HCID 24689350, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (5.9 g, 15.4 mmol), pyrrolidine (3.2 g, 16.8 mmol) and diisopropylethylamine (5.4 mL, 42.2 mmol) was added to a suspension of 3-((tert-butoxycarbonyl)amino)propanoic acid (1.0 g, 14.0 mmol) in dichloromethane (20 mL) and the resulting mixture was stirred at ambient temperature for 6 hours. TLC analysis showed no acid remaining so the mixture was diluted with dichloromethane and washed with water and brine. The organic layer was separated, dried (Na2SO4), filtered and the solvent was removed to afford a solid. The crude material was purified by silica gel chromatography using a 70:30 mixture of hexane and ethyl acetate as eluent to afford the title product as a solid (3.0 g, 88% yield). MS m/z: 243.26 [M+H]+.

Workup

  1. washwashed with water and brine
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent was removed
  6. customto afford a solid
  7. customThe crude material was purified by silica gel chromatography
  8. additiona 70:30 mixture of hexane and ethyl acetate as eluent

Sources & evidence

ORD record
ord-dd65662d5ed144cea1d9623c409fe900
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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