Water → HCID 117759754, compound

HRID 1049566Notes

Reaction equation

HRID 1049566 reaction equation
CC[N:3]=C=NCCCN(C)C.[CH2:12]([O:14][C:15](=[O:50])[CH2:16][CH:17]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][O:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[C:40]([O:42][CH3:43])[CH:39]=[CH:38][C:37]=3[F:44])=[C:32]([CH2:45][C:46]([CH3:49])([CH3:48])[CH3:47])[CH:31]=2)[CH:23]=1)[CH2:18][C:19](O)=[O:20])[CH3:13].C(N(CC)CC)C.O>CN(C=O)C>[NH2:3][C:19](=[O:20])[CH2:18][CH:17]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][O:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[C:40]([O:42][CH3:43])[CH:39]=[CH:38][C:37]=3[F:44])=[C:32]([CH2:45][C:46]([CH3:49])([CH3:48])[CH3:47])[CH:31]=2)[CH:23]=1)[CH2:16][C:15]([O:14][CH2:12][CH3:13])=[O:50]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 117760160HCID 117760160, compound

Product 1

HCID 117759754HCID 117759754, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere, WSC (53.6 mg) was added to a suspension of 5-ethoxy-3-(3-(((2′-fluoro-5′-methoxy-2-neopentyl-[1,1′-biphenyl]-4-yl)oxy)methyl)phenyl)-5-oxopentanoic acid (100 mg), 1-hydroxybenzotriazole monohydrate-ammonia complex (42.5 mg) and triethylamine (78 μL) in DMF (1 mL), and the mixture was stirred at room temperature for 2 hr. Water was added to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (47.1 mg) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e6c41034cfc14d0f9a70df1713e8031e
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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