Sodium Hydroxide → HCID 178491570, compound

HRID 350525Notes

Reaction equation

HRID 350525 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 1 N 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 1 N HCl. The mixture was concentrated in vacuo. The residue was purified by column chromatography on silica gel with MeOH—CH2C2 (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−; 1H-NMR (DMSO-d6) δ 1.38–2.00 (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—CH2C2 (1:5

Sources & evidence

ORD record
ord-b320c2a2dfcc4636a4f1192073eda334
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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