Ethyl Acetate → HCID 20189993, compound

HRID 1788829Notes

Reaction equation

HRID 1788829 reaction equation
[Br: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(OCC)(=O)C>C(O)(=O)C.S(=O)(=O)(O)O>[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]([C:8]1[CH:7]=[C:5]([OH:6])[C:4]([OH:9])=[CH:3][C:2]=1[Br:1])[C:24]([OH:26])=[O:25])=[O:21]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium Carbonate2×HCID 284874-BromocatecholHCID 12882021HCID 12882021, compound

Product 1

HCID 20189993HCID 20189993, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Procedure

4-Bromocatechol (4.77 g, 25.2 mmole) was added to an ice bath cooled suspension of N-(2,3-dioxo-4-ethylpiperazin-1-yl-carbonyl)-2-hydroxyglycine (2.59 g. 10 mmole) in glacial acetic acid (9 ml) and concentrated sulphuric acid (1 ml). The mixture was stirred for 18 hours then poured onto a mixture of ice, saturated sodium carbonate and ethyl acetate and adjusted to pH7 with sodium carbonate. The aqueous layer was collected, washed with ethyl acetate (50 ml), acidified to pH1 and extracted with ethyl acetate (3×50 ml). The extracts were dried and evaporated in vacuo to a buff solid, 2.4 g, 79%, δ[(CD3)2CO]1.13(3H, t, J7 Hz, CH2CH3), 3.57(2H, q, J7 Hz, CH2CH3), 3.5-4.3(4H, m, 2×NCH2), 5.3-7.6(3H, broad, 2×OH, CO2H), 5.73 (1H, d, J6.5 Hz, CHNH), 6.87 and 7.03 (2H, 2×s, Ar), 9.73(1H, d, J6.5 Hz, CHNH).

Workup

  1. temperaturecooled
  2. customThe aqueous layer was collected
  3. washwashed with ethyl acetate (50 ml)
  4. extractionextracted with ethyl acetate (3×50 ml)
  5. customThe extracts were dried
  6. customevaporated in vacuo to a buff solid, 2.4 g, 79%, δ[(CD3)2CO]1

Sources & evidence

ORD record
ord-114a2a5a1d2948c59ca0ec05a0544bd0
Source dataset
uspto-grants-1987_08
Patent number
US04684639

Reaction notes

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