Hydrochloric Acid → HCID 20737809, compound

HRID 354423Notes

Reaction equation

HRID 354423 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[Br:33])=[O:25])=[C:19]([O:34][CH3:35])[CH:18]=2)[C@H:13]([CH2:37][O:38][C:39]2[CH:48]=[CH:47][C:42]([C:43]([O:45]C)=[O:44])=[CH:41][CH:40]=2)[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[Br:33])=[O:25])=[C:19]([O:34][CH3:35])[CH:18]=2)[C@H:13]([CH2:37][O:38][C:39]2[CH:40]=[CH:41][C:42]([C:43]([OH:45])=[O:44])=[CH:47][CH:48]=2)[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 20737845HCID 20737845, compound

Product 1

HCID 20737809HCID 20737809, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of methyl 4-[5-(R)-benzyloxymethyl-1-[4-[N′-(2-bromophenyl)ureido]-3-methoxyphenylacetyl]-2-(S)-pyrrolidinylmethoxy]benzoate (178 mg, 0.25 mmol) in MeOH-THF (2:5, 7 ml) was added 1.0M-NaOH (750 ml, 0.75 mmol) at rt, and the resulting mixture was heated at 80° C. with stirring for 1.5 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 (15:1) as eluent to give 128 (159 mg, 91%) as a colorless amorphous solid MW 702.59 1H-NMR (CD3OD), mixture of rotamars δ1.88-2.35 (series of m, 4 H), 3.51-4.49 (series of m, 8 H), 3.64 and 3.72 (s, total 3 H), 4.87 (s, 2 H), 6.65-8.05 (series of m, 16 H); MS (ESI) m/z, 702 (M+), 704 (M++2); Anal. Calcd. for C36H36BrN3O7.H2O: C, 60.00; H, 5.32; N, 5.83. Found: C, 59.66; H, 5.04; N, 5.65.

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 (15:1) as eluent
  6. customto give

Sources & evidence

ORD record
ord-87d1c91d15f141bf838522de7a535d49
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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