Triethylamine → HCID 118092805, compound

HRID 2207418Notes

Reaction equation

HRID 2207418 reaction equation
C(N(CC)CC)C.[NH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].[Br:15][C:16]1[CH:17]=[CH:18][C:19]([S:22](Cl)(=[O:24])=[O:23])=[N:20][CH:21]=1>ClCCl.[NH4+].[Cl-]>[Br:15][C:16]1[CH:17]=[CH:18][C:19]([S:22]([NH:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:24])=[O:23])=[N:20][CH:21]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 12176Glycine ethyl esterHCID 445580975-Bromopyridine-2-sulfonyl chloride

Product 1

HCID 118092805HCID 118092805, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

Triethylamine (543 μL, 3.90 mmol) followed by ethyl glycinate (161 mg, 1.56 mmol) were added to a solution of 5-bromopyridine-2-sulfonyl chloride (200 mg, 0.780 mmol) in dichloromethane (2.6 mL) was added. The reaction mixture was stirred at room temperature and was monitored by LCMS. Upon completion, the reaction was diluted with saturated aqueous NH4Cl and the organic layer was dried over sodium sulfate and was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (10% MeOH in DCM:hexanes) to yield ethyl N-[(5-bromopyridin-2-yl)sulfonyl]glycinate. MS APCI calc'd for C9H12BrN2O4S [M+H]+ 323 and 325. found 323 and 325.

Workup

  1. additionwas added
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. concentrationwas concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (10% MeOH in DCM:hexanes)

Sources & evidence

ORD record
ord-154f10d96c764919a610bfffab352cd6
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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