Triphenylphosphine → N-(2,2-Diphenylethyl)-N-(2-chloro-3-trifluoromethylbenzyl)-2,2-dimethyl-3-(3-aminopropoxy)phenylpropionic Acid

HRID 229121Notes

Reaction equation

HRID 229121 reaction equation
[CH3:1][C:2](C)([CH2:7][C:8]1C=C[CH:11]=[C:10](O)[CH:9]=1)[C:3]([O:5]C)=[O:4].[C:16]1([CH:22]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:23][N:24]([CH2:37][CH2:38][CH2:39][OH:40])[CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[C:27]=2[Cl:36])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(O[CH:77]([CH3:79])[CH3:78])=O)=O)C>C1COCC1.O>[C:41]1([CH:22]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:23][N:24]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:34])([F:35])[F:33])[C:27]=2[Cl:36])[CH2:37][CH2:38][CH2:39][O:40][C:11]2[C:77]([CH3:78])([CH3:79])[CH:7]([CH:2]([CH3:1])[C:3]([OH:5])=[O:4])[CH:8]=[CH:9][CH:10]=2)[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 577571173-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propan-1-olHCID 67520417Methyl 2,2-dimethyl-3-(3-hydroxyphenyl)propionate

Product 1

HCID 68864466N-(2,2-Diphenylethyl)-N-(2-chloro-3-trifluoromethylbenzyl)-2,2-dimethyl-3-(3-aminopropoxy)phenylpropionic AcidYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2,2-dimethyl-3-(3-hydroxyphenyl)propionate (135 mg, 0.65 mmol) and N-(2,2-diphenylethyl)-N-(2-chloro-3-trifluoromethylbenzyl)-3-hydroxypropylamine (290 mg, 0.65 mmol) in THF (8 mL) was treated with Ph3P (170 mg, 0.65 mmol), diisopropylazodicarboxylate (135 mg, 0.65 mmol), and stirred for 16 h. The reaction was diluted with H2O and extracted with Et2O. The extracts were washed with H2O, dried, and concentrated. Purification via silica gel column chromatography eluted with 30% EtOAc:hexane yielded the titled compound (200 mg, 50%). MS (ESI) 639 (M+H+).

Workup

  1. extractionextracted with Et2O
  2. washThe extracts were washed with H2O
  3. customdried
  4. concentrationconcentrated
  5. customPurification via silica gel column chromatography
  6. washeluted with 30% EtOAc

Sources & evidence

ORD record
ord-958175d07f5c4b8c9fbd1e1ffcded43c
Source dataset
uspto-grants-2009_07
Patent number
US07560586B2

Reaction notes

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