Sodium Hydroxide → {4-[(2S)-2-benzoylamino-2-(4-phenyl-butylcarbamoyl)-ethyl]-phenoxy}-[2-(1-methyl-1-phenyl-ethyl)-2H-tetrazol-5-yl]-acetic acid

HRID 1356209Notes

Reaction equation

HRID 1356209 reaction equation
C([O:3][C:4](=[O:51])[CH:5]([O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C@H:28]([NH:42][C:43](=[O:50])[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:29](=[O:41])[NH:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:23][CH:22]=1)[C:6]1[N:7]=[N:8][N:9]([C:11]([CH3:19])([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:12])[N:10]=1)C.[OH-].[Na+]>CCO.CCOC(C)=O.O.Cl>[C:43]([NH:42][C@H:28]([C:29](=[O:41])[NH:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:27][C:24]1[CH:23]=[CH:22][C:21]([O:20][CH:5]([C:6]2[N:7]=[N:8][N:9]([C:11]([CH3:19])([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH3:12])[N:10]=2)[C:4]([OH:51])=[O:3])=[CH:26][CH:25]=1)(=[O:50])[C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1

Participants

7

Reactant 2

HCID 14798Sodium HydroxideHCID 69129258{4-[(2S)-2-benzoylamino-2-(4-phenyl-butylcarbamoyl)-ethyl]-phenoxy}-[2-(1-methyl-1-phenyl-ethyl)-2H-tetrazol-5-yl]-acetic acid ethyl ester

Product 1

HCID 69129259{4-[(2S)-2-benzoylamino-2-(4-phenyl-butylcarbamoyl)-ethyl]-phenoxy}-[2-(1-methyl-1-phenyl-ethyl)-2H-tetrazol-5-yl]-acetic acid

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of {4-[(2S)-2-benzoylamino-2-(4-phenyl-butylcarbamoyl)-ethyl]-phenoxy}-[2-(1methyl-1-phenyl-ethyl)-2H-tetrazol-5-yl]-acetic acid ethyl ester of Step C (0.070 g, 0.10 mmol) in EtOH (2 mL) is treated with 2 N NaOH (1 mL). After 1.5 h, the reaction is diluted with EtOAc, water and 10% HCl and the layers separated. The organic layer is washed with water and brine, dried (MgSO4) and concentrated to provide {4-[(2S)-2-benzoylamino-2-(4-phenyl-butylcarbamoyl)-ethyl]-phenoxy}-[2-(1-methyl-1-phenyl-ethyl)-2H-tetrazol-5-yl]-acetic acid which is used without further purification.

Workup

  1. customthe layers separated
  2. washThe organic layer is washed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-91b1fd9e288148b2b7c039f8e7569a67
Source dataset
uspto-grants-2003_07
Patent number
US06586467B2

Reaction notes

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