Hydrochloric Acid → HCID 10740202, compound

HRID 2294802Notes

Reaction equation

HRID 2294802 reaction equation
[C:1]1([NH:7][CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:12]([C:19]1[CH:24]=[CH:23][C:22]([S:25]([N:28]=[C:29]=[O:30])(=[O:27])=[O:26])=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.ClCC(OCC)=O.Cl>O1CCCC1>[O:12]([C:19]1[CH:24]=[CH:23][C:22]([S:25]([N:28]2[C:9](=[O:11])[CH2:8][N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:29]2=[O:30])(=[O:27])=[O:26])=[CH:21][CH:20]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7751Ethyl chloroacetateHCID 8471TriethylamineHCID 66025N-PhenylglycineHCID 21472161HCID 21472161, compound

Product 1

HCID 10740202HCID 10740202, compoundYield 9.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1.25 g (8.29 mmol) of N-phenylaminoacetic acid in 100 ml of tetrahydrofuran, 2.0 g (8.29 mmol) of 4-phenoxybenzenesulfonyl isocyanate were added at room temperature, and the resultant mixture was stirred for 16 hours. After completion of the reaction, the liquid reaction mixture was cooled to 0° C. and added with 2.09 g (20.7 mmol) of triethylamine and 900 mg (8.29 mmol) of ethyl chloroacetate, followed by stirring at 0° C. for 1 hour. After completion of the reaction, the liquid reaction mixture was added with 40 ml of 1N hydrochloric acid and 60 ml of saturated saline and subjected to extraction with ethyl acetate. After washing the resultant extract with water, it was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The thus-obtained crude product was purified by column chromatography on silica gel (hexane/ethyl acetate=3:1) and subjected to crystallization from hexane/ethyl acetate, thereby obtaining 310 mg (yield: 9.2%) of the title compound.

Workup

  1. customAfter completion of the reaction
  2. customthe liquid reaction mixture
  3. customAfter completion of the reaction
  4. customthe liquid reaction mixture
  5. extractionsubjected to extraction with ethyl acetate
  6. washAfter washing the resultant
  7. extractionextract with water, it
  8. dry with materialwas dried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe thus-obtained crude product
  11. customwas purified by column chromatography on silica gel (hexane/ethyl acetate=3:1)
  12. customsubjected to crystallization from hexane/ethyl acetate

Sources & evidence

ORD record
ord-579d1febe5234f0dbd7e8603c37a718e
Source dataset
uspto-grants-1997_11
Patent number
US05691335

Reaction notes

Loading…