Sodium Hydroxide → HCID 11795781, compound

HRID 1596365Notes

Reaction equation

HRID 1596365 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]1[N:18]=[C:17]([CH2:19][CH3:20])[C:16]2[CH:21]=[CH:22][CH:23]=[C:24]([CH3:25])[C:15]=2[N:14]([CH2:26][C:27]([O:29]CC)=[O:28])[C:13]1=[O:32])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>COCCOC.C(OCC)(=O)C.Cl>[CH2:1]([O:8][C:9]([NH:11][CH:12]1[N:18]=[C:17]([CH2:19][CH3:20])[C:16]2[CH:21]=[CH:22][CH:23]=[C:24]([CH3:25])[C:15]=2[N:14]([CH2:26][C:27]([OH:29])=[O:28])[C:13]1=[O:32])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 10526954HCID 10526954, compound

Product 1

HCID 11795781HCID 11795781, compoundYield 84.2%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (3RS)-3-benzyloxycarbonylamino-2,3-dihydro-5-ethyl-1-ethoxycarbonylmethyl-9-methyl-1H-1,4-benzodiazepin-2-one (1.55 g) and 1N sodium hydroxide (7.0 ml) in 1,2-dimethoxyethane (10 ml) was stirred at room temperature overnight. The reaction mixture was evaporated in vacuo to afford a residue, which was dissolved in a mixture of ethyl acetate and 1N aqueous hydrochloric acid. The separated organic layer was washed with water and brine, and then dried over magnesium sulfate. The solvent was evaporated in vacuo to afford a residue, which was triturated in diisopropyl ether and collected by filtration to give (3RS)-3-benzyloxycarbonylamino-5-ethyl-1-carboxymethyl-2,3-dihydro-9-methyl-1H-1,4-benzodiazepin-2-one (1.22 g, 84.2% yield) as a white crystalline powder.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customto afford a residue, which
  3. washThe separated organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customto afford a residue, which
  7. customwas triturated in diisopropyl ether
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-13a4391021e6454ebbe5619430182286
Source dataset
uspto-grants-2001_09
Patent number
US06291452B1

Reaction notes

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