Hydroxylamine → HCID 53890749, compound

HRID 2083996Notes

Reaction equation

HRID 2083996 reaction equation
[OH:1][NH:2][C:3](=[O:23])[CH:4]([OH:22])[CH2:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:11][CH:10]=1)(=[O:8])=[O:7].C1COCC1.NO>CO>[OH:1][NH:2][C:3](=[O:23])[C@@H:4]([OH:22])[CH2:5][S:6]([C:9]1[CH:10]=[CH:11][C:12]([O:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:13][CH:14]=1)(=[O:7])=[O:8]

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 8028TetrahydrofuranHCID 22732208HCID 22732208, compound

Product 1

HCID 53890749HCID 53890749, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Part F: To a solution of the sulfone of part E (3.9 g, 11.6 mmol) in methanol (20 mL) and THF (20 mL) was added 50% aqueous hydroxylamine (14 mL). The solution was stirred for 18 hours at ambient temperature. The solution was concentrated in vacuo and recrystallization (acetone/H2O) provided (R)-N,2-dihydroxy-3-[(4-phenoxyphenyl)sulfonyl]propanamide as a white solid (2.6 g, 67%). HPLC purity: 99%. HRMS calculated for C15H15NO6S: 338.0698, found: 338.0673.

Workup

  1. concentrationThe solution was concentrated in vacuo and recrystallization (acetone/H2O)

Sources & evidence

ORD record
ord-2a3b542ad1bf4530b247ef5cc8335b98
Source dataset
uspto-grants-2004_04
Patent number
US06716844B2

Reaction notes

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