Sodium Hydroxide → HCID 44461305, compound

HRID 63718Notes

Reaction equation

HRID 63718 reaction equation
C[O:2][C:3](=[O:36])[C@@H:4]([NH:23][C:24]([C:26]1([CH2:31][CH2:32][N:33]=[N+:34]=[N-:35])[CH2:30][CH2:29][CH2:28][CH2:27]1)=[O:25])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:22])[C:14]2[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:21])=[CH:8][CH:7]=1.[OH-].[Na+]>C1COCC1.C(O)C.O>[N:33]([CH2:32][CH2:31][C:26]1([C:24]([NH:23][C@@H:4]([CH2:5][C:6]2[CH:7]=[CH:8][C:9]([NH:12][C:13](=[O:22])[C:14]3[C:15]([Cl:21])=[CH:16][CH:17]=[CH:18][C:19]=3[Cl:20])=[CH:10][CH:11]=2)[C:3]([OH:36])=[O:2])=[O:25])[CH2:30][CH2:29][CH2:28][CH2:27]1)=[N+:34]=[N-:35]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 54226348(S)-2-[[1-(2-azidoethyl)cyclopentanecarbonyl]amino]3-[4-(2,6-dichlorobenzoylamino)phenyl]propionic acid methyl ester

Product 1

HCID 44461305HCID 44461305, compoundYield 93.1%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of (S)-2-[[1-(2-azidoethyl)cyclopentanecarbonyl]amino]-3-[4-(2,6-dichlorobenzoylamino)phenyl]propionic acid methyl ester (14.77 g, 27.7 mmol) in THF (200 mL) and ethanol (200 mL) was added aqueous 1.0N sodium hydroxide (150 mL) at room temperature. The mixture was stirred for 15 h at room temperature at which time TLC analysis of the mixture indicated the absence of starting material. Then, it was diluted with water (20 mL) and the THF and ethanol were removed by rotary evaporation and diluted with 100 mL of water and extracted with ether (200 mL) to remove any neutral impurities. The aqueous layer was neutralized with 1N HCl and the resulting white solids were collected by filtration and washed with water and hexanes. After air-drying, 13.37 g (93% yield) of (S)-2-[[1-(2-azidoethyl)cyclopentanecarbonyl]amino]-3-[4-(2,6-dichlorobenzoylamino)phenyl]propionic acid was obtained as a white solid. ES(+)-HRMS m/e calcd. for C24H25Cl2N5O4 (M+Na)+ 540.1176, obsd. 540.1177.

Workup

  1. customthe THF and ethanol were removed by rotary evaporation
  2. additiondiluted with 100 mL of water
  3. extractionextracted with ether (200 mL)
  4. customto remove any neutral impurities
  5. filtrationthe resulting white solids were collected by filtration
  6. washwashed with water and hexanes
  7. customAfter air-drying

Sources & evidence

ORD record
ord-2c4849f46c174d14ae86d9630ef521cc
Source dataset
uspto-grants-2016_09
Patent number
US09447035B2

Reaction notes

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