Lithium hydroxide, monohydrate → HCID 18405572, compound

HRID 1018313Notes

Reaction equation

HRID 1018313 reaction equation
C[O:2][C:3](=[O:37])[C:4]1[CH:13]=[C:12]([NH:14][C:15]([C:17]2[N:18]=[CH:19][N:20]([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:21]=2[CH2:22][CH:23]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:16])[CH:11]=[C:6]([C:7]([O:9]C)=[O:8])[CH:5]=1.C1COCC1.CO.O.[OH-].[Li+]>O>[CH2:30]([N:20]1[C:21]([CH2:22][CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]2)=[C:17]([C:15]([NH:14][C:12]2[CH:11]=[C:6]([C:7]([OH:9])=[O:8])[CH:5]=[C:4]([CH:13]=2)[C:3]([OH:37])=[O:2])=[O:16])[N:18]=[CH:19]1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 21899815MeOH tetrahydrofuranHCID 70161367HCID 70161367, compound

Product 1

HCID 18405572HCID 18405572, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of the product of step c above (110 mg, 0.22 mmol) in 1:1 THF/methanol (2 ml) was added the solution of lithium hydroxide monohydrate (30 mg, 0.66 mmol) in water (1 ml). The solution was stirred at room temperature for 16 h, concentrated under reduced pressure, diluted with water (1 ml) and acidified (pH=2.0, 1M HCl). The precipitate was collected by filtration, washed with water and dried to afford the title compound as a white solid (92 mg, 89%). 1H NMR (300 MHz, d6-DMSO) 13.00 (2H, br s), 10.23 (1H, s), 8.64 (2H, s), 8.15 (1H, s), 7.92 (1H, s), 7.32 (3H, m), 7.14 (2H, m), 5.28 (2H, s), 2.83 (2H, d), 1.51 (5H, m), 1.37 (4H, m), 1.14 (4H, m). The acid was converted to the di(N-methyl-D-glucamine) salt and lyophilised from water/dioxan. Found: C, 54.47; H, 7.63; N, 7.59%; C41H63N5O15.2.2 H2O requires: C, 54.35; H, 7.50; N, 7.73%.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additiondiluted with water (1 ml)
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-6777dba9abe34be9968223203e9a2f7e
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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