Water → N-Hydroxy-2-(6-methoxy-1,3,4,9-tetrahydro-beta-carboline-2-sulfonylmethyl)-3-methylbutyramide

HRID 1582045Notes

Reaction equation

HRID 1582045 reaction equation
Cl.CN(C)CCCN=C=NCC.[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23]1[CH2:22][N:21]([S:28]([CH2:31][CH:32]([CH:36]([CH3:38])[CH3:37])[C:33]([OH:35])=O)(=[O:30])=[O:29])[CH2:20][CH2:19][C:18]2=1.[Si]([O:46][NH2:47])(C(C)(C)C)(C)C.O>ClCCl>[OH:46][NH:47][C:33](=[O:35])[CH:32]([CH2:31][S:28]([N:21]1[CH2:20][CH2:19][C:18]2[C:17]3[C:25](=[CH:26][CH:27]=[C:15]([O:14][CH3:13])[CH:16]=3)[NH:24][C:23]=2[CH2:22]1)(=[O:29])=[O:30])[CH:36]([CH3:38])[CH3:37]

Participants

6

Reactant 4

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 4691350O-(tert-Butyldimethylsilyl)hydroxylamineHCID 101778142-(6-Methoxy-1,3,4,9-tetrahydro-beta-carboline-2-sulfonylmethyl)-3-methylbutyric acid

Product 1

HCID 10272029N-Hydroxy-2-(6-methoxy-1,3,4,9-tetrahydro-beta-carboline-2-sulfonylmethyl)-3-methylbutyramideYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (104 mg) was added to a slurry of 2-(6-methoxy-1,3,4,9-tetrahydro-β-carboline-2-sulfonylmethyl)-3-methylbutyric acid (172 mg) in dichloromethane (10 ml). The mixture was stirred for 5 minutes before addition of O-(t-butyldimethylsilyl)hydroxylamine (80 mg), then for 1.5 h. The mixture was poured into water (10 ml) and extracted with dichloromethane (3×15 ml). The combined organics were washed with water (2×50 ml), dried (MgSO4) and evaporated under reduced pressure. The residue was dissolved in dichloromethane (10 ml) and 1.0N hydrogen chloride in ether (2.5 ml) was added. The mixture was stirred at room temperature for 2 h. It was evaporated under reduced pressure and the residue chromatographed (SiO2, 5% methanol in dichloromethane) to give the title compound (37 mg, 21%) as a pale orange solid.

Workup

  1. extractionextracted with dichloromethane (3×15 ml)
  2. washThe combined organics were washed with water (2×50 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure
  5. dissolutionThe residue was dissolved in dichloromethane (10 ml)
  6. addition1.0N hydrogen chloride in ether (2.5 ml) was added
  7. customIt was evaporated under reduced pressure
  8. customthe residue chromatographed (SiO2, 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-0287a690b71447aca00e2f440ce7ba8d
Source dataset
uspto-grants-2004_05
Patent number
US06734189B2

Reaction notes

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