Benzoic Acid → HCID 66671286, compound

HRID 2371109Notes

Reaction equation

HRID 2371109 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:17]([O:24][C:25]([NH:27][CH2:28][CH2:29][CH:30]([CH:38](O)[CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][C:44]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[CH:43][CH:42]=1)[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.ClCCl.O>[C:1]([O:9][CH:38]([CH2:39][CH2:40][C:41]1[CH:42]=[CH:43][C:44]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[CH:45][CH:46]=1)[CH:30]([C:31]([O:33][C:34]([CH3:36])([CH3:37])[CH3:35])=[O:32])[CH2:29][CH2:28][NH:27][C:25]([O:24][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:26])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 243Benzoic AcidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66671372HCID 66671372, compound

Product 1

HCID 66671286HCID 66671286, compoundYield 74.6%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Benzoic acid (48.5 mg), 4-dimethylaminopyridine (24.3 mg) and triethylamine (0.08 ml) were added to a solution of tert-butyl 2-(2-{[(benzyloxy)carbonyl]amino}ethyl)-5-biphenyl-4-yl-3-hydroxypentanoate (200 mg) in dichloromethane (5 ml) at 0° C. and the reaction mixture was stirred for 15 minutes. 1-Ethyl-3-(3′-dimethylaminopropyl)-carbodiimide (152 mg) was added and the reaction mixture was stirred overnight. The reaction mixture was taken in distill water and extracted with dichloromethane (20 ml). The organic layer was washed with dilute sodium bicarbonate solution, brine solution, dried over anhydrous sodium sulphate and evaporated under vacuum. The residue thus obtained was purified by column chromatography using 10% ethyl acetate in hexane as eluent to furnish the title compound (180 mg).

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. extractionextracted with dichloromethane (20 ml)
  3. washThe organic layer was washed with dilute sodium bicarbonate solution, brine solution
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated under vacuum
  6. customThe residue thus obtained
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-604810ff0bc1461e987ca625dd371fa9
Source dataset
uspto-grants-2014_04
Patent number
US08710261B2

Reaction notes

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