Triphenylphosphine → HCID 18341549, compound

HRID 982837Notes

Reaction equation

HRID 982837 reaction equation
[CH2:1]([N:8]([CH2:12][C@@H:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N:21]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[S:22]([CH3:25])(=[O:24])=[O:23])[CH:16]=1)[OH:14])[CH2:9][CH2:10]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:52]N1C(=O)CCC1=O>C(Cl)Cl>[CH2:1]([N:8]([CH2:12][C@@H:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N:21]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[S:22]([CH3:25])(=[O:24])=[O:23])[CH:16]=1)[OH:14])[CH2:9][CH2:10][Br:52])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 11351508HCID 11351508, compound

Product 1

HCID 18341549HCID 18341549, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

(R)-2-[N′-Benzyl-N′-(2-hydroxyethyl)amino]-1-[3-(N-benzyl-N-methylsulfonylamino)phenyl]ethanol (173 mg; synthesized according to the process described in WO 01/04092) and triphenylphosphine (103 mg) were dissolved in dehydrated methylene chloride (5 mL), followed by stirring at −20° C. N-Bromosuccinimide (69.9 mg) was added at a stretch and the resulting mixture was stirred for 10 minutes. The reaction mixture was purified by silica gel column chromatography (5:1-3:1 hexane/ethyl acetate) to yield (R)-2-[N′-benzyl-N′-(2-bromoethyl)amino]-1-[3-(N-benzyl-N-methylsulfonylamino)phenyl]ethanol. This was immediately dissolved in acetonitrile (2.5 mL). The compound (79.8 mg; obtained in the above step B) and an aqueous 1 N sodium hydroxide solution (392 μL) were added, followed by stirring at room temperature for 14 hours. The reaction mixture was concentrated and the residue was purified by silica gel column chromatography (4:1-2:1 hexane/ethyl acetate) to yield the title compound (132.2 mg).

Workup

  1. customsynthesized
  2. stirringthe resulting mixture was stirred for 10 minutes
  3. customThe reaction mixture was purified by silica gel column chromatography (5:1-3:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b5c78477a991491c89dbbfb2f61c5ebe
Source dataset
uspto-grants-2005_03
Patent number
US06861444B2

Reaction notes

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