Diethyl Ether → HCID 9938867, compound

HRID 1459887Notes

Reaction equation

HRID 1459887 reaction equation
C([O:5][C:6](=[O:49])[CH:7]([CH2:25][C:26]1([C:32](=[O:48])[NH:33][CH:34]([C:44](=[O:47])[NH:45][CH3:46])[CH2:35][C:36]2[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=2)[CH2:31][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.CCOCC>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:32](=[O:48])[NH:33][CH:34]([C:44](=[O:47])[NH:45][CH3:46])[CH2:35][C:36]2[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=2)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1)[C:6]([OH:49])=[O:5]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 86753502HCID 86753502, compound

Product 1

HCID 9938867HCID 9938867, 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]cyclohexylmethyl}butyricacidtert-butyl ester (diastereomer A) (50 mg, 0.075 mmol) in trifluoroacetic acid (1 mL) was stirred overnight at room temperature. The solvent was evaporated under vacuum leaving a white foam which was titrated with ether to afford 4-(1,3-dioxo-1,3-dihydrobenzo[f]isoindol-2-yl)-2-{1-[2-(4-methoxyphenyl)-1-(methylcarbamoyl) ethylcarbamoyl]-cyclohexylmethyl}butyric acid (diastereomer A) as a white solid, 40 mg (87%). High Resolution Mass Spectrum M+ calculated for C35H39N3O7 : 613.2788; found: 613.2746.

Workup

  1. customThe solvent was evaporated under vacuum
  2. customleaving a white foam which

Sources & evidence

ORD record
ord-9dac960f0a4341208c4e989b15a8d040
Source dataset
uspto-grants-1998_12
Patent number
US05854275

Reaction notes

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