Hydrochloric Acid → HCID 57713882, compound

HRID 1984046Notes

Reaction equation

HRID 1984046 reaction equation
[NH:1]1[CH2:4][CH2:3][CH2:2]1.Cl.C(N(CC)CC)C.Cl[S:14]([C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=1[NH:26][CH3:27])[C:20]([OH:22])=[O:21])(=[O:16])=[O:15]>C(OCC)(=O)C>[N:1]1([S:14]([C:17]2[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=2[NH:26][CH3:27])[C:20]([OH:22])=[O:21])(=[O:16])=[O:15])[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10422AzetidineHCID 57713890HCID 57713890, compound

Product 1

HCID 57713882HCID 57713882, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Azetidine Ae (HCl salt) (0.2 g, 2 mmol) was dissolved in ethyl acetate (8 mL). Triethylamine (0.3 mL, 2 mmol) and 3-(chlorosulfonyl)-4-(methylamino)benzoic acid (1.2, 0.1 g, 0.5 mmol) were added. The reaction was left to stir for 4 hours, then extracted with 0.5 M HCl, washed with water and brine, and dried over magnesium sulfate. The ethyl acetate was evaporated and 3-(azetidin-1-ylsulfonyl)-4-(methylamino)-benzoic acid (1.3.Ae) was obtained (0.08 g, 60% yield). MS analysis (m−1)=269.

Workup

  1. waitThe reaction was left
  2. extractionextracted with 0.5 M HCl
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe ethyl acetate was evaporated

Sources & evidence

ORD record
ord-311152a95de846d8b6310194385aa00a
Source dataset
uspto-grants-2009_06
Patent number
US07544676B2

Reaction notes

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