Hydrochloric Acid → HCID 18678912, compound

HRID 1634697Notes

Reaction equation

HRID 1634697 reaction equation
[NH2:1][OH:2].[CH2:3]([N:11]([S:19]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)(=[O:21])=[O:20])[CH2:12][CH2:13][C:14](OCC)=[O:15])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl>C(OCC)C>[OH:2][NH:1][C:14](=[O:15])[CH2:13][CH2:12][N:11]([CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[S:19]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 18678882HCID 18678882, compound

Product 1

HCID 18678912HCID 18678912, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Freshly prepared hydroxylamine reagent (20 mL; 20 mmol) was added to ethyl 3-[(phenethyl)-(4-methoxy-benzenesulfonyl)-amino]-propionate (3.30 g; 9.1 mmol) and the resulting mixture stirred for 18 h at room temperature. The mixture was poured into 1 N HCl (100 mL) and extracted with CH2Cl2 (2×100 mL). The combined extracts were washed with saturated aqueous NaCl (1×100 mL), dried over MgSO4, and evaporated under reduced pressure to give a crude gum. Trituration with diethyl ether afforded 2.23 g (65%) of the title compound as an off-white solid. 300 MHz 1H-NMR (DMSO-d6): δ 2.23 (t, 2H), 2.74 (m, 2H), 3.23 (m, 2H), 3.34 (m, 2H), 3.83 (s, 3H), 7.11 (d, 2H), 7.15-7.34 (m, 5H), 7.72 (d, 2H), 8.78 (s, 1H), 10.50 (s, 1H).

Workup

  1. extractionextracted with CH2Cl2 (2×100 mL)
  2. washThe combined extracts were washed with saturated aqueous NaCl (1×100 mL)
  3. dry with materialdried over MgSO4
  4. customevaporated under reduced pressure
  5. customto give a crude gum

Sources & evidence

ORD record
ord-a187da58c8e843a6b42197dd35902d70
Source dataset
uspto-grants-2003_01
Patent number
US06506936B1

Reaction notes

Loading…