Hydroxylamine → HCID 11604459, compound

HRID 888222Notes

Reaction equation

HRID 888222 reaction equation
CC1(C)[O:6][C:5](=O)[C@H:4]([C@@H:8]([C:13]([N:15]2[CH2:20][CH2:19][N:18]([C:21]3[S:25][N:24]=[C:23]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:22]=3)[CH2:17][CH2:16]2)=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11])[O:3]1.[NH2:33][OH:34]>CC(O)C>[OH:34][NH:33][C:5](=[O:6])[C@@H:4]([OH:3])[C@@H:8]([C:13]([N:15]1[CH2:16][CH2:17][N:18]([C:21]2[S:25][N:24]=[C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:22]=2)[CH2:19][CH2:20]1)=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 58487953(5S)-2,2-dimethyl-5-((1S)-3-methyl-1-{[4-(3-phenyl-1,2,4-thiadiazol-5-yl)-1-piperazinyl]carbonyl}butyl)-1,3-dioxolan-4-one

Product 1

HCID 11604459HCID 11604459, compoundYield 109.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of (5S)-2,2-dimethyl-5-((1S)-3-methyl-1-{[4-(3-phenyl-1,2,4-thiadiazol-5-yl)-1-piperazinyl]carbonyl}butyl)-1,3-dioxolan-4-one (9.0 mg; 0.019 mmol; 1.0 eq.) in iPrOH (0.20 mL) was added an aqueous solution of hydroxylamine (50%; 0.0029 mL; 0.098 mmol; 5.0 eq.) and the resulting reaction mixture was stirred at RT for 2 h. Evaporation of the solvents gave the title product (2) as a colorless oil (9 mg; 100%). M−(ESI): 432.1; M+(ESI): 434.3. HPLC (Condition A): Rt: 3.1 min (HPLC purity: 79.3%).

Workup

  1. customthe resulting reaction mixture
  2. customEvaporation of the solvents

Sources & evidence

ORD record
ord-d9548f48aa4d4426b65fb9677b17f2f7
Source dataset
uspto-grants-2012_08
Patent number
US08247437B2

Reaction notes

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