4-Methylmorpholine → HCID 86611572, compound

HRID 1517170Notes

Reaction equation

HRID 1517170 reaction equation
[OH:1][N:2]=[C:3]([CH3:52])[C:4]([NH:7][CH2:8][CH2:9][CH:10]([CH2:42][CH2:43][NH:44][C:45]([CH3:51])([CH3:50])[C:46](=[N:48][OH:49])[CH3:47])[CH2:11][CH2:12][NH:13][C:14]([C:16]1[CH:41]=[CH:40][C:19]([CH2:20][N:21]([S:29]([C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[CH:22]([CH:26]([CH3:28])[CH3:27])[C:23](O)=[O:24])=[CH:18][CH:17]=1)=[O:15])([CH3:6])[CH3:5].CN1CCOCC1.C1CN([P+]([O:76][N:77]2N=NC3C=CC=NC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[Si](ON)(C(C)(C)C)(C)C>CN(C)C=O>[OH:76][NH:77][C:23]([CH:22]([N:21]([CH2:20][C:19]1[CH:18]=[CH:17][C:16]([C:14]([NH:13][CH2:12][CH2:11][CH:10]([CH2:42][CH2:43][NH:44][C:45]([CH3:50])([CH3:51])[C:46](=[N:48][OH:49])[CH3:47])[CH2:9][CH2:8][NH:7][C:4]([CH3:5])([CH3:6])[C:3](=[N:2][OH:1])[CH3:52])=[O:15])=[CH:41][CH:40]=1)[S:29]([C:32]1[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=1)(=[O:31])=[O:30])[CH:26]([CH3:28])[CH3:27])=[O:24]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 4691350O-(tert-Butyldimethylsilyl)hydroxylamineHCID 11038641((7-Azabenzotriazol-1-YL)oxy)tris(pyrrolidino)phosphonium hexafluorophosphateHCID 86611570HCID 86611570, compound

Product 1

HCID 86611572HCID 86611572, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The hydroxamic acid was attached via tert-butyldimethylsilyl protected intermediate (Compound 11*). Thus, a mixture of the acid (Compound 10*) (57 mg, 0.76 mmol), 4-methylmorpholine (34 μl, 0.30 mmol), [7-azabenzotriazol-1-yloxytris(pyrrolidino)phosphonium-hexafluorophosphate] PyAOP, 40 mg, 0.076 mmol) and O-(tert-butyldimethylsilyl)hydroxylamine (12 mg, 0.08 mmol) in dimethylformamide (4 ml) was stirred at ambient temperature and the reaction monitored by HPLC. The reaction was stopped after 3 hours and solvents were evaporated. The residue was re-dissolved in dichloromethane and at ambient temperature, hydrochloric acid gas was bubbled through the mixture for 10 minutes. The mixture was evaporated to dryness and the residue co-evaporated with dichloromethane (5×5 ml). The product was obtained as a white powder after HPLC, M+H, 762. Yield 15 mg.

Workup

  1. customsolvents were evaporated
  2. dissolutionThe residue was re-dissolved in dichloromethane and at ambient temperature
  3. customhydrochloric acid gas was bubbled through the mixture for 10 minutes
  4. customThe mixture was evaporated to dryness
  5. customThe product was obtained as a white powder after HPLC, M+H, 762

Sources & evidence

ORD record
ord-ce5712d8a7f64f2f9bcdfbcbd3d1e651
Source dataset
uspto-grants-2012_07
Patent number
US08231858B2

Reaction notes

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