Hydrochloric Acid → HCID 136451803, compound

HRID 1596372Notes

Reaction equation

HRID 1596372 reaction equation
C([O:3][C:4]([CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]1[C:20]2[C:21]([CH3:25])=[CH:22][CH:23]=[CH:24][C:19]=2[C:18]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[F:32])=[N:17][C:16]([CH:67]=[C:68]=[O:69])([NH:33][C:34]([NH:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([C:43]3[N:47](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:46]=[N:45][N:44]=3)[CH:38]=2)=[O:35])[C:15]1=[O:70])=[O:5])C.[OH-].[Na+].Cl.O>COCCOC.C(OCC)(=O)C>[F:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[C:18]1[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:20]=2[N:14]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][CH2:6][C:4]([OH:5])=[O:3])[C:15](=[O:70])[C:16]([CH:67]=[C:68]=[O:69])([NH:33][C:34]([NH:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([C:43]3[NH:47][N:46]=[N:45][N:44]=3)[CH:38]=2)=[O:35])[N:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 88162378HCID 88162378, compound

Product 1

HCID 136451803HCID 136451803, compoundYield 47.5%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of N-[(3RS)-1-(2-ethoxycabonylmethoxyphenyl)-carbonylmethyl-2,3-dihydro-5-(2-fluorophenyl)-9-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl]-N′-{3-[1-(triphenylmethyl)tetrazol-5-yl]phenyl}urea (196 mg) and 1N NaOH in 1,2-dimethoxyethane (2 ml) was stirred at room temperature overnight. 4N-HCl in ethyl acetate (2 ml) was added to the reaction mixture and stirred at room temperature for three days. Ethyl acetate and water were added to the reaction mixture. The separated organic layer was washed with water and brine successively, and dried over magnesium sulfate. Removal of the solvent in vacuo afforded N-[(3RS)-2,3-dihydro-5-(2-fluorophenyl)-1-(2-carboxymethoxyphenyl)-carbonylmethyl-9-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl]-N′-[3-(tetrazol-5-yl)phenyl]urea (66.0 mg, 47.4%).

Workup

  1. stirringstirred at room temperature for three days
  2. washThe separated organic layer was washed with water and brine successively
  3. dry with materialdried over magnesium sulfate
  4. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-fb345c473ce4424fadb25934419c4ead
Source dataset
uspto-grants-2001_09
Patent number
US06291452B1

Reaction notes

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