Water → HCID 86584578, compound

HRID 1061425Notes

Reaction equation

HRID 1061425 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:13][CH:12]([OH:14])[CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:15][S:16](Cl)(=[O:18])=[O:17].O>N1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:11][CH:12]([O:14][S:16]([CH3:15])(=[O:18])=[O:17])[CH2:13]2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 22220480HCID 22220480, compound

Product 1

HCID 86584578HCID 86584578, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-(4-Nitro-phenyl)-azetidin-3-ol (which was obtained in Example 396) (5.0 g, 25.8 mmol) was added to a solution of methanesulfonyl chloride (2.2 mL, 28.3 mmol) in dry pyridine (35 mL) and stirred at room temperature overnight. Water was added and the resultant precipitate was captured on a filter, washed with water, methanol, and hexanes to give 3.72 g of the desired product as an orange solid; 1H NMR (DMSO-d6) δ3.35 (s, 3H), 4.15 (m, 3H), 4.45 (m, 2H), 5.48 (m, 1H), 6.53 (d, 2H, J=9.12 Hz), 8.09 (d, 2H, J=9.12 Hz); MS (ES) m/z: 273.5 (MH+); Anal. Calcd. for C10H12N2O5S: C, 44.1 1; H, 4.44; N, 10.29. Found: C, 44.50; H, 4.48; N, 10.64.

Workup

  1. washwashed with water, methanol, and hexanes

Sources & evidence

ORD record
ord-71453394e06e40f997f1dccd218b0e23
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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