Glutaric anhydride → 5-[((1S,2R)-1-(3,5-difluorobenzyl)-3-{[1-(3-ethylphenyl)cyclopropyl]amino}-2-hydroxypropyl)amino]-5-oxopentanoic Acid

HRID 349117

Reaction equation

HRID 349117 reaction equation
[NH2:1][CH:2]([CH2:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[CH:20]=1)[CH:3]([OH:17])[CH2:4][NH:5][C:6]1([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH3:16])[CH:10]=2)[CH2:8][CH2:7]1.[C:27]1(=[O:34])[O:33][C:31](=[O:32])[CH2:30][CH2:29][CH2:28]1>C(Cl)(Cl)Cl>[F:26][C:21]1[CH:20]=[C:19]([CH:24]=[C:23]([F:25])[CH:22]=1)[CH2:18][C@H:2]([NH:1][C:27](=[O:34])[CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])[C@H:3]([OH:17])[CH2:4][NH:5][C:6]1([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH3:16])[CH:10]=2)[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 7940Glutaric anhydrideHCID 210854823-Amino-4-(3,5-difluoro-phenyl)-1-[1-(3-ethyl-phenyl)-cyclopropylamino]-butan-2-ol

Product 1

HCID 575126575-[((1S,2R)-1-(3,5-difluorobenzyl)-3-{[1-(3-ethylphenyl)cyclopropyl]amino}-2-hydroxypropyl)amino]-5-oxopentanoic Acid

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 3-Amino-4-(3,5-difluoro-phenyl)-1-[1-(3-ethyl-phenyl)-cyclopropylamino]-butan-2-ol (0.500 g, 1.387 mmol) in chloroform (7 ml) was added TEA (0.58 ml, 4.161 mmol) with stirring under nitrogen for 30 min. To this solution was added glutaric anhydride (0.158 g, 1.387 mmol) and reaction was stirred overnight at 50° C. The reaction mixture was concentrated in vacuo, yielding the product. (ES+: 475.2)

Workup

  1. additionTo this solution was added
  2. stirringwas stirred overnight at 50° C
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customyielding the product

Sources & evidence

ORD record
ord-d16a82857eef41d0a22571e9e08a89fe
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Linked notes

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