Lithium hydroxide, monohydrate → HCID 10299631, compound

HRID 2213544Notes

Reaction equation

HRID 2213544 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:37])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([C:16]2[C:20]([CH2:21][O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:19][N:18]([C:29]3[C:34]([Cl:35])=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:36])[N:17]=2)=[O:15])[CH:8]=1>C1COCC1.O>[Cl:36][C:30]1[CH:31]=[CH:32][CH:33]=[C:34]([Cl:35])[C:29]=1[N:18]1[N:17]=[C:16]([C:14]([NH:13][C:9]2[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=2)[C:6]([OH:37])=[O:5])=[O:15])[C:20]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:19]1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 69652076HCID 69652076, compound

Product 1

HCID 10299631HCID 10299631, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Lithium hydroxide monohydrate (386 mg, 9.20 mmol) was added to a solution of the product from step d (915 mg, 1.84 mmol) in THF/water (18 mL each). The reaction mixture was stirred at ambient temperature for 18 h. The reaction mixture was partitioned between ethyl acetate (40 mL) and 2M aqueous hydrochloric acid (40 mL). The aqueous phase was discarded and the organic phase was washed with brine (40 mL) and dried (MgSO4). The filtrate was evaporated to yield the title compound (841 mg, 95%). 1H NMR (DMSO-d6) 12.9 (1H, br s), 10.9 (1H, br s), 8.51 (1H, m), 7.97 (1H, m), 7.84-7.68 (4H, m), 7.49-7.46 (1H, m), 7.32-7.26 (2H, m), 7.05-6.95 (3H, m), 5.56 (2H, s). The material was further analysed as its N-methyl D-glucamine salt. Microanalysis found: C, 52.76; H, 4.98; N, 9.99%; C23H16Cl2N4O4—C7H17NO5-0.5H2O requires: C, 52.41; H, 4.98; N, 10.17%.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (40 mL) and 2M aqueous hydrochloric acid (40 mL)
  2. washthe organic phase was washed with brine (40 mL)
  3. dry with materialdried (MgSO4)
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-5f0384a8c20d4315830610160e9016e5
Source dataset
uspto-grants-2006_09
Patent number
US07105558B2

Reaction notes

Loading…