Sodium Carbonate → HCID 20189988, compound

HRID 1788830Notes

Reaction equation

HRID 1788830 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:9])[C:5](=[CH:7][CH:8]=1)[OH:6].[O:10]=[C:11]1[C:16](=[O:17])[N:15]([CH2:18][CH3:19])[CH2:14][CH2:13][N:12]1[C:20]([NH:22][CH:23](O)[C:24]([OH:26])=[O:25])=[O:21].C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C.S(=O)(=O)(O)O.O>[OH:9][C:4]1[C:5]([OH:6])=[CH:7][C:8]([CH:23]([C:24]([OH:26])=[O:25])[NH:22][C:20]([N:12]2[CH2:13][CH2:14][N:15]([CH2:18][CH3:19])[C:16](=[O:17])[C:11]2=[O:10])=[O:21])=[C:2]([F:1])[CH:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 1604584-FluorocatecholHCID 12882021HCID 12882021, compound

Product 1

HCID 20189988HCID 20189988, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

4-Fluorocatechol (3.06 g., 24 mmole) was added to a suspension of N-(2,3-dioxo-4-ethylpiperazin-1-ylcarbonyl)-2-hydroxyglycine (3.89 g, 15 mmole) in glacial acetic acid (13.5 ml) and concentrated sulphuric acid (1.5 ml). The mixture was stirred overnight, diluted with water (50 ml), adjusted to pH6 with saturated sodium carbonate and washed with ethyl acetate (2×50 ml). The aqueous solution was acidified to pH 2.5 and extracted with ethyl acetate (5×40 ml). The combined extracts were dried and evaporated to give the crude product, 6.10 g, as a foam.

Workup

  1. washwashed with ethyl acetate (2×50 ml)
  2. extractionextracted with ethyl acetate (5×40 ml)
  3. customThe combined extracts were dried
  4. customevaporated

Sources & evidence

ORD record
ord-dea297abfbc740adb41576c657c7bfec
Source dataset
uspto-grants-1987_08
Patent number
US04684639

Reaction notes

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