Triethylamine → tert-Butyl 4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-oxopiperidine-1-carboxylate

HRID 43534Notes

Reaction equation

HRID 43534 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][C@@H:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][C@H:13]2[OH:25])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8].C(N(CC)CC)C.C(OCC)(=O)C>CS(C)=O>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:11][CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][C:13]2=[O:25])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 86648545tert-Butyl trans(+/-)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-hydroxypiperidine-1-carboxylate

Product 1

HCID 68406285tert-Butyl 4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-oxopiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

tert-Butyl trans(±)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-hydroxypiperidine-1-carboxylate obtained in Example (77b) (300 mg, 0.80 mmol) was dissolved in DMSO (3 mL). Triethylamine (1.2 mL, 8.61 mmol) and sulfur trioxide-pyridine complex (737 mg, 4.63 mmol) were added, and the mixture was stirred for 15 hours. Ethyl acetate was added, to the reaction solution. This was washed with 5% saline, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting compound was used for the next reaction without purification.

Workup

  1. washThis was washed with 5% saline
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting compound was used for the next reaction without purification

Sources & evidence

ORD record
ord-33373e034ac7488b87d433fd23a91887
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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