Water → (+/-)-tert-Butyl 3-{3-[(cyclopentyl{4-[(1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}-acetyl)amino]-2-methylphenyl}propanoate

HRID 877227Notes

Reaction equation

HRID 877227 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)[C:10]([NH:12][C:13]2[C:14]([CH3:28])=[C:15]([CH2:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:16]=[CH:17][CH:18]=2)=[O:11])=[CH:5][CH:4]=1.[CH:34]1[CH:39]=[C:38]([CH:40]=[O:41])[C:37]([CH:42]=O)=[CH:36][CH:35]=1.O>C(O)(=O)C>[CH:29]1([CH:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][N:1]3[CH2:42][C:37]4[C:38](=[CH:39][CH:34]=[CH:35][CH:36]=4)[C:40]3=[O:41])=[CH:4][CH:5]=2)[C:10]([NH:12][C:13]2[C:14]([CH3:28])=[C:15]([CH2:19][CH2:20][C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[CH:16]=[CH:17][CH:18]=2)=[O:11])[CH2:30][CH2:31][CH2:32][CH2:33]1

Participants

5

Reactant 3

HCID 962WaterHCID 4807PhthalaldehydeHCID 58136676(+/-)-Tert-butyl 3-[3-({[4-(aminomethyl)phenyl](cyclopentyl)acetyl}amino)-2-methylphenyl]propanoate

Product 1

HCID 58136664(+/-)-tert-Butyl 3-{3-[(cyclopentyl{4-[(1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}-acetyl)amino]-2-methylphenyl}propanoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

At RT, 50 mg (0.11 mmol) of (+/−)-tert-butyl 3-[3-({[4-(aminomethyl)phenyl](cyclopentyl)acetyl}amino)-2-methylphenyl]propanoate and 16.4 mg (0.12 mmol) of phthaldialdehyde were dissolved in 2.5 ml of glacial acetic acid, and the mixture was left to stand for 1 h. The reaction mixture was then poured into water and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and concentrated. The residue was purified by preparative RP-HPLC. This gave 53 mg (85% of theory) of the target compound.

Workup

  1. waitthe mixture was left
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by preparative RP-HPLC

Sources & evidence

ORD record
ord-ecd2656d1d5c4c2d9aaa8a390acf87ba
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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