Citric Acid → HCID 20066641, compound

HRID 358764Notes

Reaction equation

HRID 358764 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:27])[C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=2)[CH2:10][CH:9]1[C:28]([O:30]C)=[O:29])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:27])[C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=2)[CH2:10][CH:9]1[C:28]([OH:30])=[O:29])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 20066588HCID 20066588, compound

Product 1

HCID 20066641HCID 20066641, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of methyl 1-tert-butoxycarbon-vl-4(3,4,5-trimethoxybenzoyl)piperazine-2-carboxylate (500 mg), methanol (3 ml) and water (3 ml) is added sodium hydroxide (100 mg), which is stirred for 30 minutes at room temperature. The reaction mixture is poured into a 5% aqueous solution of citric acid, followed by extraction with dichloromethane. The organic layer is dried and then concentrated to give a crude product, which is recrystallized from ethyl acetate to afford 1-tert-butoxycarbonyl-4-(3,4,5-trimethoxy-benzoyl)piperazine-2-carboxylic acid (400 mg) as colorless crystals, m.p. 188-190° C.

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. customThe organic layer is dried
  3. concentrationconcentrated
  4. customto give a crude product, which
  5. customis recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-319945295ce7412bb864066a87efc774
Source dataset
uspto-grants-1991_03
Patent number
US04997836

Reaction notes

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