Hydrochloric Acid → HCID 15896078, compound

HRID 609669Notes

Reaction equation

HRID 609669 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 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-f5a2cf4fbb544314b2c0e6135bbd248a
Source dataset
uspto-grants-1999_12
Patent number
US05998412

Reaction notes

Loading…