Water → HCID 19920950, compound

HRID 1647701Notes

Reaction equation

HRID 1647701 reaction equation
[CH2:1]([NH:5][C:6](=O)[CH2:7][CH2:8][N:9]([CH2:13][CH2:14][C:15](=O)[NH:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:10][CH2:11][SH:12])[CH2:2][CH2:3][CH3:4].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>COCCOC.C(Cl)Cl>[CH2:17]([NH:16][CH2:15][CH2:14][CH2:13][N:9]([CH2:8][CH2:7][CH2:6][NH:5][CH2:1][CH2:2][CH2:3][CH3:4])[CH2:10][CH2:11][SH:12])[CH2:18][CH2:19][CH3:20]

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 19920939HCID 19920939, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19920950HCID 19920950, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Dissolve N-butyl-3-[(2-butylcarbamoyl-ethyl)-(2-mercapto-ethyl)-amino]-propionamide (10 mmol) prepared in Scheme VIII, step A in 1,2-dimethoxyethane (50 mL) and treat with lithium aluminum hydride (20 mmol). Heat the reaction to reflux for 18 hours. After cooling the reaction 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
  2. customthe reaction
  3. temperatureto reflux for 18 hours
  4. temperatureAfter cooling the reaction
  5. washrinse with water (100 mL), brine (100 mL)
  6. dry with materialdry over anhydrous sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate under vacuum
  9. customPurify the residue by flash chromatography (silica gel, methanol/methylene chloride)

Sources & evidence

ORD record
ord-e21f9def3d0444eaac2b81f88fe7cfb0
Source dataset
uspto-grants-1995_07
Patent number
US05434145

Reaction notes

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