Hydrochloric Acid → HCID 69333506, compound

HRID 354484Notes

Reaction equation

HRID 354484 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][NH:17][CH2:18][CH:19]([NH:42][CH:43]1[CH2:45][CH2:44]1)[C:20](=[O:41])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29]([NH:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[CH3:38])=[O:30])=[C:24]([O:39][CH3:40])[CH:23]=1)[C:6]([O:8]CC)=[O:7].[OH-].[Na+].Cl>C1COCC1.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][NH:17][CH2:18][CH:19]([NH:42][CH:43]1[CH2:44][CH2:45]1)[C:20](=[O:41])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29]([NH:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[CH3:38])=[O:30])=[C:24]([O:39][CH3:40])[CH:23]=1)[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23512328HCID 23512328, compound

Product 1

HCID 69333506HCID 69333506, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of ethyl 3-methoxy-4-[[2-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetyl]-N-[2-cyclopropylamino]ethylamino]ethoxy]benzoate (195 mg, 0.30 mmol)) in THF:MeOH(4:1, v/v) (5 mL) and 1N NaOH (0.756 mL) was stirred at 50 C. for 15 hr. The pH of the mixture was adjusted to 7.4 by the addition of 1N HCl, and extracted with CHCl3:MeOH(9:1, v/v). The extract was washed with brine, dried over MgSO4, and evaporated in vacuo. The residue was crystallized with Et2O to give 57 mg (38%) 3-methoxy-4-[[2-[3-methoxy-4-[N′-(2-methyl phenyl)ureido]phenylacetyl]-[2-cyclopropylamino]ethylamino]ethoxy]benzoic acid 264 as a white crystalline material. mp 135-140° C.; IR (KBr), 3324, 2937, 1535, 1032, 754 cm−1; 1H-NMR (CD3OD, 400 MHz) δ0.50-0.73 (m, 4H), 2.29 (s, 3H), 2.53 (m, 1H), 2.98 (m, 1H), 3.21 (m, 1H), 3.58-3.88 (m, 11H), 3.91 (s, 1H), 4.09 (m, 1H), 4.25 (m, 1H), 6.76-6.92 (m, 3H), 7.01 (m, 1H), 7.18 (m, 2H), 7.60 (m, 3H), 8.00 (d, J=8.3 Hz, 1H); MS (FAB) m/z 591(M+H)+; Anal Calcd. for C32H38N4O7.3.0H2O, C, 59.62; H, 6.88; N, 8.69. Found, C, 59.25; H, 6.29; N, 8.29.

Workup

  1. extractionextracted with CHCl3:MeOH(9:1
  2. washThe extract was washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was crystallized with Et2O

Sources & evidence

ORD record
ord-649574dc0feb4d4b8d43ded805182dd4
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

Loading…