Sodium Hydroxide → HCID 178491570, compound

HRID 354459Notes

Reaction equation

HRID 354459 reaction equation
C([O:8][C:9]([C@H:11]1[CH2:16][CH2:15][C@@H:14]([NH:17][CH2:18][CH:19]2[CH2:23][CH2:22][CH2:21][N:20]2[C:24](=[O:45])[CH2:25][C:26]2[CH:31]=[CH:30][C:29]([NH:32][C:33]([NH:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[CH3:42])=[O:34])=[C:28]([O:43][CH3:44])[CH:27]=2)[CH2:13][CH2:12]1)=[O:10])C1C=CC=CC=1.[OH-].[Na+]>C1COCC1.CO>[CH3:44][O:43][C:28]1[CH:27]=[C:26]([CH2:25][C:24]([N:20]2[CH2:21][CH2:22][CH2:23][CH:19]2[CH2:18][NH:17][C@@H:14]2[CH2:15][CH2:16][C@H:11]([C:9]([OH:10])=[O:8])[CH2:12][CH2:13]2)=[O:45])[CH:31]=[CH:30][C:29]=1[NH:32][C:33]([NH:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[CH3:42])=[O:34]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178491571HCID 178491571, compound

Product 1

HCID 178491570HCID 178491570, compoundYield 73.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of benzylcis-4-[[1-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenyl acetyl]-2-pyrrolidinyl]methylamino]cyclohexanecarboxylate (1.5 g, 2.45 mmol) in THF (10.0 ml) and MeOH (5.0 ml) was added 1N NaOH (3.68 ml, 3.68 mmol). The mixture was stirred at 70° C. for 18 hr. The mixture was concentrated in vacuo, water was added thereto, and neutralized with 1N HCl. The mixture was concentrated in vacuo. The residue was purified by column chromatography on silica gel with MeOH—CH2Cl2 (1:5, v/v) as eluent to give cis-4-[[1-[3-methoxy-4-[N′-(2-methyl phenyl)ureido]phenylacetyl]-2-pyrrolidinyl]methylamino]cyclohexanecarboxylic acid 171 (940 mg, 73%) as an amorphous solid. MW 522.64 IR (KBr) 3283, 2945, 2860, 1534, 1453, 1415 cm−1; 1H-NMR (DMSO-d6) δ1.38-2.00 (m, 12H), 2.45 (s, 3H), 2.30-3.95 (m, 4H), 3.22-3.75 (m, 2H), 3.58 (s, 2H), 3.86 (s, 3H), 4.12 (m, 1H), 6.73-7.16 (m, 5H), 7.77-7.79 (m, 1H), 7.98-8.02 (m, 1H), 8.51-8.52 (m, 1H), 8.57-8.59 (m, 1H); MS (FAB) m/z 523 (M++1); Anal. Calcd. for C29H38N4O5.0.5NaCl.2.2H2O: C, 58.89; H, 7.23; N, 9.47. Found: C, 59.21; H, 7.11; N, 9.11.

Workup

  1. concentrationThe mixture was concentrated in vacuo, water
  2. additionwas added
  3. concentrationThe mixture was concentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel with MeOH—CH2Cl2 (1:5

Sources & evidence

ORD record
ord-b34b882b556a4ac4a5959272d40e8315
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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