Hydrochloric Acid → HCID 9885413, compound

HRID 1634695Notes

Reaction equation

HRID 1634695 reaction equation
[NH2:1][OH:2].[CH2:3]([N:10]([S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH2:11][CH2:12][C:13](OCC)=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl>C(OCC)C>[OH:2][NH:1][C:13](=[O:14])[CH2:12][CH2:11][N:10]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 5063708HCID 5063708, compound

Product 1

HCID 9885413HCID 9885413, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Freshly prepared hydroxylamine reagent (20 mL; 20 mmol) was added to ethyl 3-[(benzyl)-(4-methoxybenzenesulfonyl)-amino]-propionate (3.30 g; 8.8 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 (2×10 mL). The combined extracts were washed with saturated aqueous NaCl (1×10 mL), dried over MgSO4, and evaporated under reduced pressure to give a crude gum. Trituration with diethyl ether afforded 2.33 g (68%) of the title compound as an off-white solid. 300 MHz 1H-NMR (DMSO-d6): δ 2.06 (m, 2H), 3.25 (m, 2H), 3.87 (s, 3H), 4.33 (s, 2H), 7.16 (d, 2H), 7.20-7.42 (m, 5H), 7.80 (d, 2H), 8.70 (bs, 1H), 10.38 (s, 1H).

Workup

  1. extractionextracted with CH2Cl2 (2×10 mL)
  2. washThe combined extracts were washed with saturated aqueous NaCl (1×10 mL)
  3. dry with materialdried over MgSO4
  4. customevaporated under reduced pressure
  5. customto give a crude gum

Sources & evidence

ORD record
ord-8fd0c7312368434a87b5e35cca804fbb
Source dataset
uspto-grants-2003_01
Patent number
US06506936B1

Reaction notes

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