Water → HCID 19920944, compound

HRID 1647699Notes

Reaction equation

HRID 1647699 reaction equation
C1(S([N:10]([CH2:20][CH2:21][CH2:22][N:23]([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:24][CH2:25][SH:26])[CH2:11][CH2:12][C:13]([NH:15][CH2:16][CH2:17][CH2:18][CH3:19])=O)(=O)=O)C=CC=CC=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>COCCOC.C(Cl)Cl>[CH2:27]([N:23]([CH2:22][CH2:21][CH2:20][NH:10][CH2:11][CH2:12][CH2:13][NH:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:24][CH2:25][SH:26])[CH2:28][CH2:29][CH3:30]

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 23202531HCID 23202531, compound

Product 1

HCID 19920944HCID 19920944, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Dissolve 3-(benzenesulfonyl-{3-[butyl-(2-mercapto-ethyl)-amino]-propyl}-amino)-N-butyl-proponamide (10 mmol) prepared in Scheme VII, step B in 1,2-dimethoxyethane (50 mL) and treat with lithium aluminum hydride (20 mmol). Heat the re action to reflux for 18 hours. After cooling the react ion is worked up by consecutive addition of water (0.8 mL), 10% sodium hydroxide (1.2 mL) and water (2 .2 mL). Then dilute with methylene chloride (200 mL), rinse with water (100 mL), brine (100 mL), dry over anhydrous sodium sulfate, filter and concentrate under vacuum. Purify the residue by flash chromatography (silica gel, methanol/methylene chloride) to provide the title compound.

Workup

  1. temperatureHeat the re action
  2. temperatureto reflux for 18 hours
  3. temperatureAfter cooling the react ion
  4. washrinse with water (100 mL), brine (100 mL)
  5. dry with materialdry over anhydrous sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under vacuum
  8. customPurify the residue by flash chromatography (silica gel, methanol/methylene chloride)

Sources & evidence

ORD record
ord-b85c5fd8971d40fea5c001a2a94f6bb7
Source dataset
uspto-grants-1995_07
Patent number
US05434145

Reaction notes

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