Hexane → (R)-(-)-1-tert-butylcarbonylmethyl-2-oxo-3-amino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine oxalate monohydrate

HRID 352378Notes

Reaction equation

HRID 352378 reaction equation
[C:1]([C:5]([CH2:7][N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:11][C@@H:10]([NH2:25])[C:9]1=[O:26])=[O:6])([CH3:4])([CH3:3])[CH3:2].O.O.[C:29]([OH:34])(=[O:33])[C:30]([OH:32])=[O:31].CCCCCC>C(OCC)(=O)C>[OH2:6].[C:29]([OH:34])(=[O:33])[C:30]([OH:32])=[O:31].[C:1]([C:5]([CH2:7][N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:11][C@@H:10]([NH2:25])[C:9]1=[O:26])=[O:6])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8058HexaneHCID 61373Oxalic acid dihydrateHCID 11190074(R)-1-tert-butylcarbonylmethyl-2-oxo-3-amino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Product 1

HCID 69908115(R)-(-)-1-tert-butylcarbonylmethyl-2-oxo-3-amino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine oxalate monohydrate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The (R)-(−)-1-tert-butylcarbonylmethyl-2-oxo-3-amino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine thus obtained was dissolved in 550 ml of ethyl acetate. To the resulting solution was added 16.31 g of oxalic acid dihydrate to dissolve the latter in the former. Then, 367 ml of n-hexane was added and the mixture was stirred overnight. Crystals so precipitated were collected by filtration with suction, washed with a mixed solvent of ethyl acetate and n-hexane (1:1), and then dried, whereby 55 g of (R)-(−)-1-tert-butylcarbonylmethyl-2-oxo-3-amino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine oxalate monohydrate was obtained.

Workup

  1. dissolutionto dissolve the latter in the former
  2. customCrystals so precipitated
  3. filtrationwere collected by filtration with suction
  4. washwashed with a mixed solvent of ethyl acetate and n-hexane (1:1)
  5. customdried

Sources & evidence

ORD record
ord-53137785b67747058d2bdf6f5d0cced2
Source dataset
uspto-grants-2004_06
Patent number
US06747022B2

Reaction notes

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