Triethylamine → HCID 68809404, compound

HRID 434298Notes

Reaction equation

HRID 434298 reaction equation
[C:1]([O:5][C:6](=[O:33])[NH:7][C@H:8]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=1)[CH2:9][N:10]1[CH2:15][CH2:14][CH:13]([C:16](=[O:24])[C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:12][CH2:11]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:41][S:42](Cl)(=[O:44])=[O:43]>ClCCl>[C:1]([O:5][C:6](=[O:33])[NH:7][C@H:8]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][S:42]([CH3:41])(=[O:44])=[O:43])=[CH:28][CH:27]=1)[CH2:9][N:10]1[CH2:11][CH2:12][CH:13]([C:16](=[O:24])[C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)[CH2:14][CH2:15]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68809401HCID 68809401, compound

Product 1

HCID 68809404HCID 68809404, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ((R)-1-(4-amino-benzyl)-2-[4-(4-fluoro-benzoyl)-piperidin-1-yl]-ethyl)-carbamic acid tert-butyl ester (1.19 g, 2.61 mmol) in dichloromethane (15 ml) cooled to 0° C. is added triethylamine (0.37 ml, 2.65 mmol) and methanesulfonylchloride (0.192 ml, 2.49mmol). The reaction mixture is allowed to warm to ambient temperature with stirring for 1 hour, then washed with water and saturated brine solution, dried over magnesium sulphate and evaporated. The crude product is purified by flash silica chromatography (ethylacetate:hexane gradient 6:4 to 1:0 elution) to afford [(R)-2-[4-(4-fluoro-benzoyl)-piperidin-1-yl]-1-(4-methanesulfonylamino-benzyl)-ethyl]-carbamic acid tert-butyl ester. [MH]+534.7.

Workup

  1. washwashed with water and saturated brine solution
  2. dry with materialdried over magnesium sulphate
  3. customevaporated
  4. customThe crude product is purified by flash silica chromatography (ethylacetate:hexane gradient 6:4 to 1:0 elution)

Sources & evidence

ORD record
ord-0ee28b6ea0d5432181226c426ef54563
Source dataset
uspto-grants-2003_12
Patent number
US06670379B2

Reaction notes

Loading…