Carbodiimide → HCID 59852591, compound

HRID 2373811Notes

Reaction equation

HRID 2373811 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)=[CH:13][C:12]([C:25](O)=[O:26])=[C:11]([OH:28])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N=C=N.[Cl:32][C:33]1[CH:34]=[C:35]([C:40]2[CH:45]=[CH:44][C:43]([CH2:46][C@@H:47]([NH2:54])[C:48]3[O:52][N:51]=[C:50]([CH3:53])[N:49]=3)=[CH:42][CH:41]=2)[CH:36]=[CH:37][C:38]=1[F:39]>C1COCC1.ClCCCl>[Cl:32][C:33]1[CH:34]=[C:35]([C:40]2[CH:45]=[CH:44][C:43]([CH2:46][C@@H:47]([NH:54][C:25]([C:12]3[CH:13]=[C:14]([C:15]4[CH:16]=[CH:17][C:18]([C:21]([F:22])([F:24])[F:23])=[CH:19][CH:20]=4)[C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[CH:10][C:11]=3[OH:28])=[O:26])[C:48]3[O:52][N:51]=[C:50]([CH3:53])[N:49]=3)=[CH:42][CH:41]=2)[CH:36]=[CH:37][C:38]=1[F:39]

Participants

5

Reactant 3

HCID 160435CarbodiimideHCID 68869453HCID 68869453, compoundHCID 68869955HCID 68869955, compound

Product 1

HCID 59852591HCID 59852591, compoundYield 20.6%

Reagents, catalysts & solvents 1

HCID 21493386Dce thfSolvent

Procedure

To a solution of 6-Benzyloxy-4-hydroxy-4′-trifluoromethyl-biphenyl-3-carboxylic acid (52 mg, 0.13 mmol) in THF:DCE (1:1, 2 mL) was added PS-Carbodiimide resin (0.14 g, 1.3 mmol/g) and 2-(3′-Chloro-4′-fluoro-biphenyl-4-yl)-1-(R)-(3-methyl-[1,2,4]oxadiazol-5-yl)-ethylamine (0.03 g, 0.09 mmol) and stirred for 12 h, resin was filtered and washed with EtOAc (5 mL), filtrate was concentrated and silicagel chromatography of the residue gave pure 6-Benzyloxy-4-hydroxy-4′-trifluoromethyl-biphenyl-3-carboxylic acid [2-(3′-chloro-4′-fluoro-biphenyl-4-yl)-1-(R)-(3-methyl-[1,2,4]oxadiazol-5-yl)-ethyl]-amide (0.013 g).

Workup

  1. filtrationresin was filtered
  2. washwashed with EtOAc (5 mL), filtrate
  3. concentrationwas concentrated

Sources & evidence

ORD record
ord-a99dc20af157482d9713b53de29b4817
Source dataset
uspto-grants-2008_12
Patent number
US07459472B2

Reaction notes

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