Hydrochloric Acid → HCID 9928357, compound

HRID 1634696Notes

Reaction equation

HRID 1634696 reaction equation
[NH2:1][OH:2].[C:3]1([N:9]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:10][CH2:11][C:12](OCC)=[O:13])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl>C(OCC)C>[OH:2][NH:1][C:12](=[O:13])[CH2:11][CH2:10][N:9]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 18678887HCID 18678887, compound

Product 1

HCID 9928357HCID 9928357, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Freshly prepared hydroxylamine reagent (20 mL; 20 mmol) was added to ethyl 3-[(phenyl)-(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 2.14 g (68%) of the title compound as an off-white solid. 300 MHz 1H-NMR (DMSO-d6): δ 2.12 (t, 2H), 3.74 (t, 2H), 3.86 (s, 3H), 7.03 (d, 2H), 7.08 (d, 2H), 7.32 (m, 3H), 7.47 (d, 2H), 8.74 (s, 1H), 10.35 (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-e02f0e4c90784f94aafbfbd77d73f7b4
Source dataset
uspto-grants-2003_01
Patent number
US06506936B1

Reaction notes

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