Carbon tetrabromide → Tert-butyl 3-[3-({[4-(bromomethyl)phenyl](cyclopentyl)acetyl}amino)-2-methylphenyl]propanoate

HRID 877191Notes

Reaction equation

HRID 877191 reaction equation
[CH:1]1([CH:6]([C:26]2[CH:31]=[CH:30][C:29]([CH2:32]O)=[CH:28][CH:27]=2)[C:7]([NH:9][C:10]2[C:11]([CH3:25])=[C:12]([CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:13]=[CH:14][CH:15]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(Br)(Br)(Br)[Br:35].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Br:35][CH2:32][C:29]1[CH:30]=[CH:31][C:26]([CH:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[C:7]([NH:9][C:10]2[C:11]([CH3:25])=[C:12]([CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH:13]=[CH:14][CH:15]=2)=[O:8])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 58136762tert-Butyl(+/-)-3-[3-({cyclopentyl[4-(hydroxymethyl)phenyl]acetyl}amino)-2-methylphenyl]propanoate

Product 1

HCID 58136306Tert-butyl 3-[3-({[4-(bromomethyl)phenyl](cyclopentyl)acetyl}amino)-2-methylphenyl]propanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.0 g (13.29 mmol) of tert-butyl(+/−)-3-[3-({cyclopentyl[4-(hydroxymethyl)phenyl]acetyl}amino)-2-methylphenyl]propanoate were dissolved in 375 ml of dry THF, and 9.25 g (27.9 mmol) of carbon tetrabromide were added. Over a period of 1.5 h, 9.06 g (34.54 mmol) of triphenylphosphine were then added in small portions. The reaction mixture was stirred at RT for 5 h, and the solid was then filtered off and the filtrate was concentrated. The residue was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 5:1→1:1). This gave 7.22 g (about 100% of theory, purity about 95%) of the title compound.

Workup

  1. filtrationthe solid was then filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 5:1→1:1)

Sources & evidence

ORD record
ord-e0388d68aaaa44ec95623a6070270039
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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