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

HRID 992436Notes

Reaction equation

HRID 992436 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-e01db50124bf41b3bccdf7c6ed395f49
Source dataset
uspto-grants-2002_10
Patent number
US06469020B2

Reaction notes

Loading…