(3-(((tert-Butoxycarbonyl)amino)(phenyl)methyl)phenoxy)acetic acid → 3-(1,3-Dioxolan-2-yl)propyl 4-(5-((3-(((tert-butoxycarbonyl)amino)(phenyl)-methyl)phenoxy)methyl)-1,2,4-oxadiazol-3-yl)benzoate

HRID 332710Notes

Reaction equation

HRID 332710 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=1)[O:13][CH2:14][C:15](O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:27][N:28]=[C:29]([C:31]1[CH:47]=[CH:46][C:34]([C:35]([O:37][CH2:38][CH2:39][CH2:40][CH:41]2[O:45][CH2:44][CH2:43][O:42]2)=[O:36])=[CH:33][CH:32]=1)[NH2:30]>C(#N)C.N1C=CC=CC=1.[Cl-].[Na+].O>[C:1]([O:5][C:6]([NH:8][CH:9]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=1)[O:13][CH2:14][C:15]1[O:27][N:28]=[C:29]([C:31]2[CH:32]=[CH:33][C:34]([C:35]([O:37][CH2:38][CH2:39][CH2:40][CH:41]3[O:42][CH2:43][CH2:44][O:45]3)=[O:36])=[CH:46][CH:47]=2)[N:30]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 2

HCID 71093126(3-(((tert-Butoxycarbonyl)amino)(phenyl)methyl)phenoxy)acetic acidHCID 866769173-(1,3-Dioxolan-2-yl)propyl 4-(N'-hydroxycarbamimidoyl)benzoate

Product 1

HCID 710933303-(1,3-Dioxolan-2-yl)propyl 4-(5-((3-(((tert-butoxycarbonyl)amino)(phenyl)-methyl)phenoxy)methyl)-1,2,4-oxadiazol-3-yl)benzoate

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6342AcetonitrileSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 2-(3-(((tert-butoxycarbonyl)amino)(phenyl)methyl)phenoxy)-acetic acid (0.087 g. 0.34 mmol) and 3-(1,3-dioxolan-2-yl)propyl 4-(N′-hydroxy-carbamimidoyl)benzoate (0.10 g, 0.28 mmol) in acetonitrile (1 mL), was added 1-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (0.087 g, 0.42 mmol). The reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was diluted with pyridine and heated at 150° C. for 30 minutes in a microwave. The reaction was diluted with saturated brine and extracted with ethyl acetate (×3). The combined organic fractions were dried with magnesium sulfate, and the solvent evaporated at reduced pressure. The material was used directly in the next step without further purification (0.142 g, 87%).

Workup

  1. temperatureheated at 150° C. for 30 minutes in a microwave
  2. extractionextracted with ethyl acetate (×3)
  3. dry with materialThe combined organic fractions were dried with magnesium sulfate
  4. customthe solvent evaporated at reduced pressure
  5. customThe material was used directly in the next step without further purification (0.142 g, 87%)

Sources & evidence

ORD record
ord-520e471813b34074baff470229cc5986
Source dataset
uspto-grants-2014_11
Patent number
US08877774B2

Reaction notes

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