4-Methylmorpholine → HCID 22612471, compound

HRID 343972Notes

Reaction equation

HRID 343972 reaction equation
CN(C)C(C[C:6]([NH:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)(=[O:16])=[O:15])([CH:10]([CH3:12])[CH3:11])[C:7]([OH:9])=O)=O.O.[OH:27][N:28]1C2C=CC=CC=2N=N1.Cl.[CH3:38][N:39]([CH3:48])[CH2:40][CH2:41]CN=C=NCC.Cl.NO.CN1CC[O:56]CC1>CN(C)C=O>[CH3:38][N:39]([CH3:48])[C:40]([CH2:41][N:13]([S:14]([C:17]1[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=1)(=[O:15])=[O:16])[CH:6]([CH:10]([CH3:11])[CH3:12])[C:7]([NH:28][OH:27])=[O:9])=[O:56]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 443297Hydroxyamine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 22612435HCID 22612435, compound

Product 1

HCID 22612471HCID 22612471, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of dimethylcarbamoylmethyl(4-methoxybenzenesulfonyl)amino-3-methylbutyric acid (1.42 grams, 3.81 mmol) and 1-hydroxybenztriazole hydrate (687 mg, 4.48 mmol) in dry dimethylformamide (7 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (974 mg, 5.08 mmol). After stirring for 30 minutes, hydroxylamine hydrochloride (1.17 grams, 16.8 mmol) and then N-methylmorpholine (2.8 mL, 25.5 mmol) were added. The mixture was stirred at room temperature overnight and then concentrated under vacuum. The residue was taken up in ethyl acetate and the resulting solution was washed sequentially with water, 0.5N hydrochloric acid solution and brine. The solution was then dried over magnesium sulfate and concentrated under vacuum to leave an oil which was chromatographed on silica gel eluting successively with ethyl acetate, 5% methanol in chloroform and 10% methanol in chloroform to afford 2-[dimethylcarbamoylmethyl(4-methoxybenzenesulfonyl)amino]-N-hydroxy-3-methylbutyramide as a white solid, 390 mg (26%). 1H NMR (DMSO-d6): δ 10.70 (br s, 1H), 8.89 (s, 1H), 7.80 (d, J=8.9 Hz, 2H), 7.10 (d, J=8.9 Hz, 2H), 4.62 (d, J=17.7 Hz, 1H), 4.14 (d, J=17.7 Hz, 1H), 3.84 (s, 3H), 3.40 (d, J=10.4 Hz, 1H), 2.97 (s, 3H), 2.82 (s, 3H), 1.88-1.72 (m, 1H), 0.72 (d, J=6.5 Hz, 6H); MS (thermospray): m/z 388 (M+1); HRMS calculated for C16H26N3O6S (M+H): 388.1542 Found: 388.1592.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. concentrationconcentrated under vacuum
  3. washthe resulting solution was washed sequentially with water, 0.5N hydrochloric acid solution and brine
  4. dry with materialThe solution was then dried over magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customto leave an oil which
  7. customwas chromatographed on silica gel eluting successively with ethyl acetate, 5% methanol in chloroform and 10% methanol in chloroform

Sources & evidence

ORD record
ord-2bfaeb29548b455c8f49a754775b10ef
Source dataset
uspto-grants-1999_01
Patent number
US05863949

Reaction notes

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