Hydrochloric Acid → HCID 15896078, compound

HRID 842986Notes

Reaction equation

HRID 842986 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH2:14]([N:21]([S:28](Cl)(=[O:30])=[O:29])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl>C(Cl)Cl>[CH2:14]([N:21]([S:28]([N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)(=[O:29])=[O:30])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 8471TriethylamineHCID 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 triethylamine (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 6 h 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. additionwas added
  2. extractionThe product was extracted into methylene chloride
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. customThe organics were removed in vacuo
  6. customthe crude product was chromatographed (PTLC, SiO2, 25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d50f833a6afe44ee8f377c25afd8c5bc
Source dataset
uspto-grants-2002_04
Patent number
US06376506B1

Reaction notes

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