Water → HCID 22987127, compound

HRID 987908Notes

Reaction equation

HRID 987908 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][N:11]([C:17](=[O:27])[CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23](=[O:26])[NH:24][N:25]=1)[CH2:12][C:13]([O:15]C)=[O:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Li+].[OH-].O>C1COCC1>[C:1]([NH:8][CH2:9][CH2:10][N:11]([C:17](=[O:27])[CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23](=[O:26])[NH:24][N:25]=1)[CH2:12][C:13]([OH:15])=[O:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 22987120HCID 22987120, compound

Product 1

HCID 22987127HCID 22987127, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl N-(2-Bocaminoethyl)-N-[3-oxo-2,3,-dihydropyridazin-6-yl-propionyl]glycinate (1.00 mmol, 382 mg) in THF (12.5 mL) was added LiOH (2M, aqueous, 2.0 mL). The solution was stirred at rt. for 15 minutes, additional water (10 mL) was added and the THF was removed in vacuo. The pH of the aqueous phase was adjusted to 3.0 by addition of HCl (2M, aqueous). The product was isolated by continuous extraction with dichloromethane (DCM) followed by evaporation in vacuo to give the desired product (215 mg, 80%) as a colorless powder (UVmax 287 nm). 1H NMR (DMSO-d6): δ 12.73 (s br and s vbr, 2H, NH and COOH), 7.38 (7.35) (d, J=9.7 Hz, 1H, arom.), 6.78 (d, J=9.7 Hz, 1H, arom.), 6.83 (6.70) (t, 1H, NH), 3.92 (4.11) (s, 2H, CH2), 3.39-3.27 (m, 2H, CH2), 3.08 (3.00) (q, 2H, CH2), 2.73-2.66 (m, 2H, CH2), 2.69-2.52 (m, 2H, CH2), 1.33 (1.36) (s, 9H, Boc). 13C NMR (DMSO-d6): δ 171.50 (171.93), 171.04 (171.38), 160.39, 155.73, 146.88 (146.92), 134.41, 129.53, 77.99 (77.76), 47.44 (49.98), 47.61 (46.64), 38.31 (37.97), 30.05 (30.40), 29.31 (29.12), 28.24. FAB+ MS: 369.14 (M+H+, calc. for C16H24N4O6+H+ 369.1774).

Workup

  1. customthe THF was removed in vacuo
  2. additionThe pH of the aqueous phase was adjusted to 3.0 by addition of HCl (2M, aqueous)
  3. customThe product was isolated by continuous extraction with dichloromethane (DCM)
  4. customfollowed by evaporation in vacuo

Sources & evidence

ORD record
ord-ab4a3c80939d4289a9a107df6475e33a
Source dataset
uspto-grants-2003_10
Patent number
US06632919B1

Reaction notes

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