HCID 86753503, compound → HCID 74972390, compound

HRID 1459890Notes

Reaction equation

HRID 1459890 reaction equation
C([O:5][C:6](=[O:48])[CH:7]([CH2:25][C:26]1([C:31](=[O:47])[NH:32][CH:33]([C:43](=[O:46])[NH:44][CH3:45])[CH2:34][C:35]2[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=2)[CH2:30][CH2:29][CH2:28][CH2:27]1)[CH2:8][CH2:9][N:10]1[C:18](=[O:19])[C:17]2[CH:16]=[C:15]3[CH:20]=[CH:21][CH:22]=[CH:23][C:14]3=[CH:13][C:12]=2[C:11]1=[O:24])(C)(C)C>FC(F)(F)C(O)=O>[O:19]=[C:18]1[C:17]2[CH:16]=[C:15]3[CH:20]=[CH:21][CH:22]=[CH:23][C:14]3=[CH:13][C:12]=2[C:11](=[O:24])[N:10]1[CH2:9][CH2:8][CH:7]([CH2:25][C:26]1([C:31](=[O:47])[NH:32][CH:33]([C:43](=[O:46])[NH:44][CH3:45])[CH2:34][C:35]2[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=2)[CH2:27][CH2:28][CH2:29][CH2:30]1)[C:6]([OH:48])=[O:5]

Participants

3

Reactant 1

HCID 86753503HCID 86753503, compound

Product 1

HCID 74972390HCID 74972390, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4-(1,3-dioxo-1,3-dihydrobenzo[f]isoindol-2-yl)-2-{1-[2-(4-methoxyphenyl)-1-(methylcarbamoyl)ethylcarbamoyl]cyclopentylmethyl}butyric acid tert-butyl ester (diastereomer A) (45 mg, 0.069 mmol) in trifluoracetic acid (1 mL) was stirred overnight at room temperature. The solvent was evaporated under vacuum leaving a white foam which was triturated with ether to afford 4-(1,3-dioxo-1,3-dihydrobenzo[f]isoindol-2-yl)-2-{1-[2-(4-methoxyphenyl)-1-(methylcarbamoyl)ethylcarbamoyl]-cyclopentylmethyl}butyric acid (diastereomer A) as a white solid, 33 mg (80%). High Resolution Mass Spectrum M+ calculated for C34H37N3O7 : 599.2632; found:

Workup

  1. customThe solvent was evaporated under vacuum
  2. customleaving a white foam which
  3. customwas triturated with ether

Sources & evidence

ORD record
ord-39d317cf0e104c1998daebd0780a1da3
Source dataset
uspto-grants-1998_12
Patent number
US05854275

Reaction notes

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