tert-butyl (2S)-2-{2-(4-fluorophenethyl)-5-[1-(thiazol-2-yl)-2-(1-methylimidazol-5-yl)ethoxy]benzoylamino}-4-methylsulfanylbutyrate → (2S)-2-{2-(4-Fluorophenethyl)-5-[1-(thiazol-2-yl)-2-(1-methylimidazol-5-yl)ethoxy]benzoylamino}-4-methylsulfanylbutyric acid

HRID 1251927Notes

Reaction equation

HRID 1251927 reaction equation
[F:1][C:2]1[CH:44]=[CH:43][C:5]([CH2:6][CH2:7][C:8]2[CH:28]=[CH:27][C:26]([O:29][CH:30]([C:38]3[S:39][CH:40]=[CH:41][N:42]=3)[CH2:31][C:32]3[N:36]([CH3:37])[CH:35]=[N:34][CH:33]=3)=[CH:25][C:9]=2[C:10]([NH:12][C@@H:13]([CH2:21][CH2:22][S:23][CH3:24])[C:14]([O:16]C(C)(C)C)=[O:15])=[O:11])=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:44]=[CH:43][C:5]([CH2:6][CH2:7][C:8]2[CH:28]=[CH:27][C:26]([O:29][CH:30]([C:38]3[S:39][CH:40]=[CH:41][N:42]=3)[CH2:31][C:32]3[N:36]([CH3:37])[CH:35]=[N:34][CH:33]=3)=[CH:25][C:9]=2[C:10]([NH:12][C@@H:13]([CH2:21][CH2:22][S:23][CH3:24])[C:14]([OH:16])=[O:15])=[O:11])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 57100633tert-butyl (2S)-2-{2-(4-fluorophenethyl)-5-[1-(thiazol-2-yl)-2-(1-methylimidazol-5-yl)ethoxy]benzoylamino}-4-methylsulfanylbutyrate

Product 1

HCID 57278593(2S)-2-{2-(4-Fluorophenethyl)-5-[1-(thiazol-2-yl)-2-(1-methylimidazol-5-yl)ethoxy]benzoylamino}-4-methylsulfanylbutyric acidYield 89%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of tert-butyl (2S)-2-{2-(4-fluorophenethyl)-5-[1-(thiazol-2-yl)-2-(1-methylimidazol-5-yl)ethoxy]benzoylamino}-4-methylsulfanylbutyrate (0.050 g, 0.078 mmol) in TFA was stirred at ambient temperature under a nitrogen atmosphere for 4 hours. The TFA was evaporated away and the residues basified with saturated sodium bicarbonate solution, reacidified with 2NHCl to pH6 and extracted with dichloromethane. The extracts were dried and evaporated to dryness. The residue was dried under high vacuum to give the title compound as a white solid (0.040 g, 89%).

Workup

  1. customThe TFA was evaporated away
  2. extractionextracted with dichloromethane
  3. customThe extracts were dried
  4. customevaporated to dryness
  5. customThe residue was dried under high vacuum

Sources & evidence

ORD record
ord-c58db41caf9e41aba7dfba50f2137d4f
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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