Hydrochloric Acid → HCID 15896078, compound

HRID 366470Notes

Reaction equation

HRID 366470 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH2:7]([N:14]([S:21](Cl)(=[O:23])=[O:22])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl>C(Cl)Cl>[CH2:7]([N:14]([S:21]([N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)(=[O:22])=[O:23])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 15896077HCID 15896077, compound

Product 1

HCID 15896078HCID 15896078, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of morpholine (1.05 ml, 12 mmol) and triethylanrine (1.84 ml, 12 mmol) in methylene chloride (10 ml) was added to a solution of ethyl 2-[benzyl-(chlorosulfonyl)-amino]acetate (2.3 g, 8.3 mmol), [prepared as described in Step 1 above], in methylene chloride (30 ml) at 0° C. The reaction mixture was slowly allowed to warm to RT and after 6h 1M HCl was added. The product was extracted into methylene chloride, washed with brine, and dried over MgSO4. The organics were removed in vacuo and the crude product was chromatographed (PTLC, SiO2, 25% ethyl acetate/hexane) to give ethyl 2-[benzyl-(morpholine-4-sulfonyl)amino]acetate as a colorless oil (6%).

Workup

  1. extractionThe product was extracted into methylene chloride
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. customThe organics were removed in vacuo
  5. customthe crude product was chromatographed (PTLC, SiO2, 25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-641ad6f987114fb987f798527eedc089
Source dataset
uspto-grants-2000_10
Patent number
US06130220

Reaction notes

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