Hydrochloric Acid → HCID 20737797, compound

HRID 350486Notes

Reaction equation

HRID 350486 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]1[N:14]([C:15](=[O:36])[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[CH3:33])=[O:25])=[C:19]([O:34][CH3:35])[CH:18]=2)[C@H:13]([CH2:37][O:38][C:39]2[CH:40]=[C:41]([CH:46]=[CH:47][CH:48]=2)[C:42]([O:44]C)=[O:43])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO.C1COCC1>[CH2:1]([O:8][CH2:9][C@@H:10]1[N:14]([C:15](=[O:36])[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[CH3:33])=[O:25])=[C:19]([O:34][CH3:35])[CH:18]=2)[C@H:13]([CH2:37][O:38][C:39]2[CH:40]=[C:41]([CH:46]=[CH:47][CH:48]=2)[C:42]([OH:44])=[O:43])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20737827HCID 20737827, compound

Product 1

HCID 20737797HCID 20737797, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of methyl 3-[5-(R)-benzyloxymethyl-1-[4-[N′-(2-methylphenyl) ureido]-3-methoxyphenylacetyl]-2-(S)-pyrrolidinylmethoxy]benzoate (185 mg, 0.28 mmol) in MeOH-THF (2:5, 7 ml) was added 1.0 M-NaOH (860 ml, 0.86 mmol) at rt, and the resulting mixture was heated at 60° C. with stirring for 1 h. The reaction mixture was poured into 1N-HCl, then extracted with CHCl3. The organic layer was washed with brine, drying over anhydrous Na2SO4, then concentrated in vacuo. The residue was chromatographed on silica gel with CHCl3-MeOH (5:1) as eluent to give129 (171 mg, 94%) as a colorless amorphous solid. MW 637.72 1H-NMR (CD3OD), mixture of rotamars δ 1.89–2.37 (series of m, 4 H), 2,29 (s, 3 H), 3.52–4.53 (series of m, 8 H), 3.66 and 3.74 (s, total 3 H), 4.85 (s, 2 H), 6.66–7.98 (series of m, 16 H); MS (ESI) m/z, 638 (M++H), 660 (M++Na+); Anal. Calcd for C37H39N3O7.H2O: C, 67.77; H, 6.30; N, 6.41. Found: C, 67.40; H, 5.95: N, 6.14.

Workup

  1. extractionextracted with CHCl3
  2. washThe organic layer was washed with brine
  3. dry with materialdrying over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel with CHCl3-MeOH (5:1) as eluent to give129 (171 mg, 94%) as a colorless amorphous solid
  6. addition(CD3OD), mixture of rotamars δ 1.89–2.37 (series of m, 4 H), 2,29 (s, 3 H), 3.52–4.53 (series of m, 8 H), 3.66 and 3.74 (s, total 3 H), 4.85 (s, 2 H), 6.66–7.98 (series of m, 16 H)

Sources & evidence

ORD record
ord-c8f4f85512ac41899edc791fd6d6be2e
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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