Hydrochloric Acid → HCID 9887686, compound

HRID 1634698Notes

Reaction equation

HRID 1634698 reaction equation
[NH2:1][OH:2].[CH3:3][O:4][C:5]1[CH:31]=[CH:30][C:8]([CH2:9][CH2:10][N:11]([S:19]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH2:12][CH2:13][C:14](OCC)=[O:15])=[CH:7][CH:6]=1.Cl>C(OCC)C>[OH:2][NH:1][C:14](=[O:15])[CH2:13][CH2:12][N:11]([CH2:10][CH2:9][C:8]1[CH:30]=[CH:31][C:5]([O:4][CH3:3])=[CH:6][CH:7]=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 18678879HCID 18678879, compound

Product 1

HCID 9887686HCID 9887686, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Freshly prepared hydroxylamine reagent (6 mL; 6 mmol) was added to ethyl 3-[(4-methoxyphenethyl)-(4-methoxybenzenesulfonyl)-amino]-propionate (587 mg; 1.40 mmol) and the resulting mixture stirred overnight at room temperature. The mixture was poured into 1 N HCl (40 mL) and extracted with CH2Cl2 (2×40 mL). The combined extracts were washed with saturated aqueous NaCl (40 mL), dried over MgSO4, and evaporated under reduced pressure to give crude product. Trituration with diethyl ether afforded 408 mg (71%) of the title compound as a white solid. 300 MHz 1H-NMR (DMSO-d6): δ 2.24 (t, 2H), 2.68 (t, 2H), 3.21 (t, 2H), 3.31 (m, 2H), 3.72 (s, 3H), 3.84 (s, 3H), 6.84 (d, 2H), 7.11 (d, 4H), 7.71 (d, 2H), 8.78 (s, 1H), 10.49 (s, 1H).

Workup

  1. extractionextracted with CH2Cl2 (2×40 mL)
  2. washThe combined extracts were washed with saturated aqueous NaCl (40 mL)
  3. dry with materialdried over MgSO4
  4. customevaporated under reduced pressure
  5. customto give crude product

Sources & evidence

ORD record
ord-4e6a5a60f3ff47d99ab31d0f5dbeb040
Source dataset
uspto-grants-2003_01
Patent number
US06506936B1

Reaction notes

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