Triethylamine → HCID 18767769, compound

HRID 2300216Notes

Reaction equation

HRID 2300216 reaction equation
[C:1]([O:5][C:6](=[O:19])[N:7]([CH:15]1[CH2:18][NH:17][CH2:16]1)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[F:27][C:28]1[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1>ClCCl>[C:1]([O:5][C:6](=[O:19])[N:7]([CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH:15]1[CH2:18][N:17]([S:34]([C:31]2[CH:32]=[CH:33][C:28]([F:27])=[CH:29][CH:30]=2)(=[O:36])=[O:35])[CH2:16]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 69950958HCID 69950958, compound

Product 1

HCID 18767769HCID 18767769, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of azetidin-3-yl-benzyl-carbamic acid tert-butyl ester (0.20 g, 0.76 mmol) in dichloromethane (2 ml) was added triethylamine (0.15 g, 1.5 mmol) followed by 4-fluorobenzenesulfonyl chloride (0.17 g, 0.84 mmol). The mixture was stirred at room temperature for 18 h. It was then quenched with 50% sodium carbonate solution and the volatiles were evaporated. The residue was diluted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, and evaporated. The crude material was washed with hexanes to give 0.29 g of a colorless gum; MS (ES) m/z 420.9 (MH+); HRMS (FAB) Calcd. for C21H26FN2O4S (MH+): 421.1597, Found: 421.1633.

Workup

  1. customIt was then quenched with 50% sodium carbonate solution
  2. customthe volatiles were evaporated
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated
  7. washThe crude material was washed with hexanes

Sources & evidence

ORD record
ord-397d998765e345ed9eb5ccf467e55f64
Source dataset
uspto-grants-2002_12
Patent number
US06498170B2

Reaction notes

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