Phenylacetic Acid → HCID 67333180, compound

HRID 1988080Notes

Reaction equation

HRID 1988080 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN=C=NCCCN(C)C.[C:22]([O:26][C:27](=[O:54])[CH:28]([NH:38][C:39]([C:41]1[CH:46]=[CH:45][C:44]([C:47]2[CH:52]=[CH:51][C:50]([NH2:53])=[CH:49][CH:48]=2)=[CH:43][CH:42]=1)=[O:40])[CH2:29][CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])([CH3:25])([CH3:24])[CH3:23].CCN(CC)CC>CN(C=O)C.CN(C1C=CN=CC=1)C>[C:22]([O:26][C:27](=[O:54])[CH:28]([NH:38][C:39]([C:41]1[CH:42]=[CH:43][C:44]([C:47]2[CH:48]=[CH:49][C:50]([NH:53][C:8](=[O:10])[CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:51][CH:52]=2)=[CH:45][CH:46]=1)=[O:40])[CH2:29][CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])([CH3:23])([CH3:24])[CH3:25]

Participants

7

Reactant 4

HCID 999Phenylacetic AcidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 67333061HCID 67333061, compound

Product 1

HCID 67333180HCID 67333180, compoundYield 12.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of phenylacetic acid (89 mg, 0.65 mmol, 1 equiv) in DMF (10 mL) was added to EDCI (188 mg, 0.98 mmol, 1.5 equiv.). After stirring for 20 min, 2-[(4′-Amino-biphenyl-4-carbonyl)-amino]-pentanedioic acid di-tert-butyl ester (297 mg, 0.65 mmol, 1 equiv.) was added, followed by the addition of Et3N (0.23 mL, 1.64 mmol, 2.5 equiv.) and DMAP (16 mg, 0.13 mmol, 20%). The reaction mixture was allowed to stir at room temperature overnight. Reaction was complete as determined by TLC. DMF was removed and the residue was dissolved in EtOAc. The organic layer was washed with H2O and brine, and then dried over MgSO4. After solvent was evaporated, the crude residue was purified by HPLC to give 45 mg of 2-[(4′-Phenylacetylamino-biphenyl-4-carbonyl)-amino]-pentanedioic acid di-tert-butyl ester in 12% yield. MS (ESI) m/z 573.

Workup

  1. stirringto stir at room temperature overnight
  2. customReaction
  3. customDMF was removed
  4. dissolutionthe residue was dissolved in EtOAc
  5. washThe organic layer was washed with H2O and brine
  6. dry with materialdried over MgSO4
  7. customAfter solvent was evaporated
  8. customthe crude residue was purified by HPLC

Sources & evidence

ORD record
ord-ea1d51ab4c5d4028937bf4690102bdae
Source dataset
uspto-grants-2009_06
Patent number
US07553873B2

Reaction notes

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