[4-(Acetoxymethyl)phenyl](cyclopentyl)acetic acid → Tert-butyl(+/-)-3-(3-{[{4-[(acetyloxy)methyl]phenyl}(cyclopentyl)-acetyl]amino}-2-methylphenyl)propanoate

HRID 877189Notes

Reaction equation

HRID 877189 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C:13]([OH:15])=O)=[CH:8][CH:7]=1)(=[O:3])[CH3:2].[NH2:21][C:22]1[C:23]([CH3:37])=[C:24]([CH2:28][CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH:25]=[CH:26][CH:27]=1>CN(C=O)C.N1C=CC=CC=1>[C:1]([O:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([CH:12]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C:13]([NH:21][C:22]2[C:23]([CH3:37])=[C:24]([CH2:28][CH2:29][C:30]([O:32][C:33]([CH3:35])([CH3:34])[CH3:36])=[O:31])[CH:25]=[CH:26][CH:27]=2)=[O:15])=[CH:10][CH:11]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 58136423[4-(Acetoxymethyl)phenyl](cyclopentyl)acetic acidHCID 58136633Tert-butyl 3-(3-amino-2-methylphenyl)propanoate

Product 1

HCID 58136347Tert-butyl(+/-)-3-(3-{[{4-[(acetyloxy)methyl]phenyl}(cyclopentyl)-acetyl]amino}-2-methylphenyl)propanoate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

11.41 g (90% pure, 37.16 mmol) of (+/−)-{4-[(acetyloxy)methyl]phenyl}(cyclopentyl)acetic acid were dissolved in a mixture of 71.8 ml of DMF and 22.5 ml of pyridine, and 15.54 g (40.88 mmol) of 1-[bis(dimethylamino)methylene]-5-chloro-3-oxy-1H-benzotriazol-1-ium tetrafluoroborate and 8.75 g (37.16 mmol) of tert-butyl 3-(3-amino-2-methylphenyl)propanoate were added. The reaction mixture was stirred at RT overnight and then concentrated under high vacuum. The residue was taken up in 100 ml of ethyl acetate and washed successively with 10% strength aqueous citric acid, saturated sodium bisulfate solution and saturated sodium chloride solution. The organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1→3:1). This gave 16.36 g (89.2% of theory) of the title compound.

Workup

  1. additionwere added
  2. concentrationconcentrated under high vacuum
  3. washwashed successively with 10% strength aqueous citric acid, saturated sodium bisulfate solution and saturated sodium chloride solution
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1→3:1)

Sources & evidence

ORD record
ord-7a277a690a884f58a97018958aabb3ac
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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