Hydroxylamine → HCID 11641261, compound

HRID 989160Notes

Reaction equation

HRID 989160 reaction equation
[ClH:1].[O:2]([C:9]1[CH:14]=[CH:13][C:12]([S:15]([CH2:18][C:19]2([C:28]([OH:30])=O)[CH2:24][CH2:23][N:22]([CH2:25][C:26]#[CH:27])[CH2:21][CH2:20]2)(=[O:17])=[O:16])=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.CN(C)CCCN=C=NCC.CN1CCOCC1.[NH2:50][OH:51]>CN(C=O)C.O>[ClH:1].[OH:51][NH:50][C:28]([C:19]1([CH2:18][S:15]([C:12]2[CH:13]=[CH:14][C:9]([O:2][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)=[CH:10][CH:11]=2)(=[O:16])=[O:17])[CH2:24][CH2:23][N:22]([CH2:25][C:26]#[CH:27])[CH2:21][CH2:20]1)=[O:30]

Participants

7

Reactant 4

HCID 787HydroxylamineHCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 131724108HCID 131724108, compound

Product 1

HCID 11641261HCID 11641261, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

Part H: To a solution of the carboxylic acid of Part G (460 mg, 1.1 mmol) in DMF (10 mL) was added N-hydroxbenzotriazole.H2O (180 mg, 1.33 mmol) and after 5 minutes of stirring was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (299 mg, 1.56 mmol). After 10 additional minutes 4-methylmorpholine (0.49 mL, 4.45 mmol) and 50% aqueous hydroxylamine (0.22 mL, 3.34 mmol) and the solution stirred for 24 hours. An additional aliquot of each reagent was added and the solution stirred for an additional 48 hours. The solution was diluted with H2O, extracted with chloroform, washed with satd. NaCl and dried over MgSO4. Reverse phase HPLC (acetonitrile/H2O) provided the hydroxamate compound as a white solid (N-hydroxy-4-[[(4-phenoxyphenyl)-sulfonyl]-methyl]-1-(2-propynyl)-4-piperidinecarboxamide, monohydrochloride; 200 mg, 42%). HRMS calc'd for C22H24N2O5S: 429.1489, found 429.1480. Anal. calc'd for C22H24N2O5S: C, 61.66; H, 5.64; N, 6.54; S, 7.48. Found: C, 61.33; H, 5.68; N, 6.36; S, 7.35.

Workup

  1. additionAn additional aliquot of each reagent was added
  2. extractionextracted with chloroform
  3. washwashed with satd
  4. dry with materialNaCl and dried over MgSO4

Sources & evidence

ORD record
ord-91bda9a5f6f04034bc154c3e789c9e86
Source dataset
uspto-grants-2003_10
Patent number
US06638952B1

Reaction notes

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