Lithium hydroxide, monohydrate → HCID 68684241, compound

HRID 2234429Notes

Reaction equation

HRID 2234429 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([NH:11][C:12]2[N:22]=[C:21]3[C:15]([N:16]([CH3:29])[C:17](=[O:28])[CH2:18][CH2:19][N:20]3[CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:14][N:13]=2)[O:9][CH:10]=1)=[O:5])C.O.[OH-].[Li+]>C1COCC1.O.CO>[CH:23]1([N:20]2[CH2:19][CH2:18][C:17](=[O:28])[N:16]([CH3:29])[C:15]3[C:21]2=[N:22][C:12]([NH:11][C:8]2[O:9][CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=2)=[N:13][CH:14]=3)[CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68685677HCID 68685677, compound2×

Product 1

HCID 68684241HCID 68684241, compoundYield 60.4%

Reagents, catalysts & solvents 3

HCID 887MethanolCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl2-[(2-cyclopentyl-6-methyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-1,3-oxazole-4-carboxylate (Intermediate 151; 160 mg, 0.40 mmol) was dissolved in THF (1 mL) and water (0.5 mL). Lithium hydroxide monohydrate (84 mg, 2.0 mmol) was added and a few drops of methanol and the mixture stirred at room temperature overnight. The mixture was neutralised with 2N HCl(aqu) and concentrated. The residue was taken up in MeOH/Water and absorbed onto an SCX column, washed with methanol/water and eluted with ammonia in methanol. Product containing fractions were concentrated, the residue taken-up in DCM, dried (MgSO4) and concentrated to give the title compound as a white solid (90 mg, 60%).

Workup

  1. concentrationconcentrated
  2. customabsorbed onto an SCX column
  3. washwashed with methanol/water
  4. washeluted with ammonia in methanol
  5. additionProduct containing fractions
  6. concentrationwere concentrated
  7. dry with materialthe residue taken-up in DCM, dried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-87971e0476944e52ab44c185eb5cba41
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

Loading…