Sodium Hydroxide → HCID 69129241, compound

HRID 1356211Notes

Reaction equation

HRID 1356211 reaction equation
C([O:3][C:4](=[O:40])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C@H:14]([NH:28][C:29](=[O:36])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:15](=[O:27])[NH:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:9][C:8]=1[N+:37]([O-:39])=[O:38])C.[OH-].[Na+]>CCO.O.CCOC(C)=O.Cl>[C:29]([NH:28][C@H:14]([C:15](=[O:27])[NH:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:40])=[O:3])=[C:8]([N+:37]([O-:39])=[O:38])[CH:9]=1)(=[O:36])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

7

Reactant 2

HCID 14798Sodium HydroxideHCID 69129495HCID 69129495, compound

Product 1

HCID 69129241HCID 69129241, compound

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of {4-[(2S)-2-benzoylamino-2-(4-phenyl-butylcarbamoyl)-ethyl]-2-nitro-phenoxy}-acetic acid ethyl ester of Step E (0.124 g, 0.226 mmol) in EtOH (2 mL) is treated with 0.5 mL of 2 N NaOH. After 1.5 h, the reaction is diluted with water, EtOAc, and 10% HCl. The layers are separated and the organic layer washed with water, and brine. The organic layer is dried (MgSO4) and concentrated under reduced pressure to provide {4-[(2S)-2-benzoylamino-2-(4-phenyl-butylcarbamoyl)-ethyl]-2-nitro-phenoxy}-acetic acid which is used without further purification.

Workup

  1. customThe layers are separated
  2. washthe organic layer washed with water, and brine
  3. dry with materialThe organic layer is dried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-70e7565a7a164ab3ba9f20e187f26d8c
Source dataset
uspto-grants-2003_07
Patent number
US06586467B2

Reaction notes

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