Triethylamine → HCID 57748831, compound

HRID 598510Notes

Reaction equation

HRID 598510 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][C@@H:8]1[CH2:12][CH2:11][NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:14][O:15][C:16]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[C:17]=1[C:18](Cl)=[O:19].CCN(CC)CC>C(Cl)Cl>[C:1]([O:5][C:6](=[O:13])[NH:7][C@@H:8]1[CH2:12][CH2:11][N:10]([C:18](=[O:19])[C:17]2[C:21]([O:25][CH3:26])=[CH:22][CH:23]=[CH:24][C:16]=2[O:15][CH3:14])[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 748102,6-Dimethoxybenzoyl chlorideHCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidine

Product 1

HCID 57748831HCID 57748831, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2.94 g (15.8 mmol) (R)-pyrrolidin-3-yl-carbamic acid tert-butyl ester (commercially available), 2,6-dimethoxybenzoyl chloride (commercially available) and 2.08 g (2.05 mmol) NEt3 in 15 mL DCM was stirred at room temperature over night. The mixture was absorbed on isolute SPE and purified by column chromatography on silica eluting with a gradient formed from heptane and ethyl acetate to yield 3.78 g (68%) of the title compound as white foam. (MH+) 351.2

Workup

  1. customThe mixture was absorbed on isolute SPE
  2. custompurified by column chromatography on silica eluting with a gradient
  3. customformed from heptane and ethyl acetate

Sources & evidence

ORD record
ord-d3f26ecc6f3f4ade962379e36b1db31b
Source dataset
uspto-grants-2011_03
Patent number
US07897627B2

Reaction notes

Loading…