Hydrochloric Acid → HCID 178424202, compound

HRID 1018328Notes

Reaction equation

HRID 1018328 reaction equation
C[O:2][C:3](=[O:37])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH2:11][C:12]2[N:13]=[C:14]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[CH3:36])[NH:15][C:16]=2[C:17](=[O:29])[NH:18][C:19]23[CH2:28][CH:23]4[CH2:24][CH:25]([CH2:27][CH:21]([CH2:22]4)[CH2:20]2)[CH2:26]3)[CH:5]=1.[OH-].[Na+].Cl>C(O)C.O>[C:19]12([NH:18][C:17]([C:16]3[NH:15][C:14]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[CH3:36])=[N:13][C:12]=3[CH2:11][CH2:10][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:37])=[O:2])=[O:29])[CH2:28][CH:23]3[CH2:22][CH:21]([CH2:27][CH:25]([CH2:24]3)[CH2:26]1)[CH2:20]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178497734HCID 178497734, compound

Product 1

HCID 178424202HCID 178424202, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of the product of step c (232 mg, 0.65 mmol) in ethanol (13 ml) was added 1M sodium hydroxide (1.3 ml, 1.3 mmol). The solution was refluxed for 2 h, diluted with water (10 ml), then acidified (pH=5, 0.01M HCl). The resulting precipitate was collected by filtration, washed with water and dried to give the title compound (271 mg, 86%). 1H NMR (300 MHz, d6-DMSO) 12.40 (1H, br s), 12.2 (1H, br s), 7.80-7.29 (8H, m), 6.98 (1H, br s), 3.23 (2H, m), 3.00 (2H, m), 2.44 (3H, s) 2.03 (9H, s), 1.65 (6H, s). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 58.98; H, 7.83; N, 7.40% C37H50N4O8.4H2O requires: C, 59.18 H, 7.79; N, 7.46%.

Workup

  1. temperatureThe solution was refluxed for 2 h
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-c5d901feb0a1481688655da5fb98986c
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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