Hydrochloric Acid → HCID 18678921, compound

HRID 1634700Notes

Reaction equation

HRID 1634700 reaction equation
[NH2:1][OH:2].[C:3]1([CH:9]([N:16]([S:24]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH2:17][CH2:18][C:19](OCC)=[O:20])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl>C(OCC)C>[OH:2][NH:1][C:19](=[O:20])[CH2:18][CH2:17][N:16]([CH:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[S:24]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 18678894HCID 18678894, compound

Product 1

HCID 18678921HCID 18678921, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Freshly prepared hydroxylamine reagent (8 mL; 8 mmol) was added to ethyl 3-[(diphenylmethyl)-(4-methoxybenzene-sulfonyl)-amino]-propionate (563 mg; 1.24 mmol) and the resulting mixture stirred overnight at room temperature. The mixture was poured into 1 N HCl (100 mL) and extracted with CH2Cl2 (2×50 mL). The combined extracts were washed with saturated aqueous NaCl (100 mL), dried over MgSO4, and evaporated under reduced pressure to give crude product. Trituration with diethyl ether afforded 262 mg (48%) of the title compound as a white solid. 300 MHz 1H-NMR (DMSO-d6): δ 1.81 (m, 2H), 3.40(m, 2H), 3.84 (s, 3H), 6.31 (s, 1H), 7.02 (m, 6H), 7.28 (m, 6H), 7.71 (d, 2H), 8.59 (s, 1H), 10.23 (s, 1H).

Workup

  1. extractionextracted with CH2Cl2 (2×50 mL)
  2. washThe combined extracts were washed with saturated aqueous NaCl (100 mL)
  3. dry with materialdried over MgSO4
  4. customevaporated under reduced pressure
  5. customto give crude product

Sources & evidence

ORD record
ord-c9decfa5ae164c1db9f5d2b4acc28b00
Source dataset
uspto-grants-2003_01
Patent number
US06506936B1

Reaction notes

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