Tetrahydrofuran → HCID 21997017, compound

HRID 1457342Notes

Reaction equation

HRID 1457342 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH2:12][CH:13]([CH2:17][S:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[C:14](O)=[O:15])(=[O:11])=[O:10])=[CH:5][CH:4]=1.Cl.CN(C)[CH2:32][CH2:33][CH2:34]N=C=NCC.Cl.C([NH:49]O)C1C=CC=CC=1.[O:51]1[CH2:55][CH2:54][CH2:53][CH2:52]1>C(Cl)(Cl)Cl>[CH2:55]([O:51][NH:49][C:14](=[O:15])[CH:13]([CH2:17][S:18]([C:21]1[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1)(=[O:20])=[O:19])[CH2:12][S:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:10])=[O:11])[C:54]1[CH:34]=[CH:33][CH:32]=[CH:52][CH:53]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11332622N-benzylhydroxylamine hydrochlorideHCID 21997023HCID 21997023, compound

Product 1

HCID 21997017HCID 21997017, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 2-(4-methoxybenzenesulfonylmethyl)-3-(4-methoxybenzenesulfonyl)-propionic acid (5.0 g, 12 mmol) in tetrahydrofuran (30 mL), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (4.3 g, 23 mmol), benzylhydroxylamine hydrochloride (2.3 g, 14 mmol), and distilled water (30 mL) is stirred overnight. The mixture is filtered to yield a white precipitate which is dissolved in chloroform (200 ml) and filtered. The filtrate is extracted with brine (100 mL) and the organic phase concentrated in vacuo, to yield N-benzyloxy-2-(4-methoxybenzenesulfonylmethyl)-3-(4-methoxybenzenesulfonyl)-propionamide (2.24 g, 36%). The initial filtrate from the overnight reaction is transferred to ethyl acetate and extracted with 10% hydrochloric acid, water, aqueous sodium bicarbonate, and brine, and concentrated in vacuo to also yield the title compound as a white solid.

Workup

  1. distillationdistilled water (30 mL)
  2. filtrationThe mixture is filtered
  3. customto yield a white precipitate which
  4. filtrationfiltered
  5. extractionThe filtrate is extracted with brine (100 mL)
  6. concentrationthe organic phase concentrated in vacuo

Sources & evidence

ORD record
ord-341478e858f54f0196df264953c73782
Source dataset
uspto-grants-1998_12
Patent number
US05847153

Reaction notes

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