Triphenylphosphine → 1-[1-Tert-butoxycarbonyl-3-(1,3-dioxo-1,3-dihydrobenzo[f]isoindol-2-yl)propylamino]cyclohexanecarboxylic acid benzyl ester

HRID 1459893Notes

Reaction equation

HRID 1459893 reaction equation
[C:1]([O:5][C:6]([CH:8]([NH:12][C:13]1([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:9][CH2:10]O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:29]=[C:30]1[C:38]2[CH:37]=[C:36]3[CH:39]=[CH:40][CH:41]=[CH:42][C:35]3=[CH:34][C:33]=2[C:32](=[O:43])[NH:31]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH2:22]([O:21][C:19]([C:13]1([NH:12][CH:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10][N:31]2[C:32](=[O:43])[C:33]3[CH:34]=[C:35]4[CH:42]=[CH:41][CH:40]=[CH:39][C:36]4=[CH:37][C:38]=3[C:30]2=[O:29])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:20])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 3351942,3-NaphthalenedicarboximideHCID 5462977Diethyl azodicarboxylateHCID 53835842Benzyl 1-(1-tert-butoxycarbonyl-3-hydroxy-1-propylamino)cyclohexanecarboxylate

Product 1

HCID 700833741-[1-Tert-butoxycarbonyl-3-(1,3-dioxo-1,3-dihydrobenzo[f]isoindol-2-yl)propylamino]cyclohexanecarboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl 1-(1-tert-butoxycarbonyl-3-hydroxy-1-propylamino)cyclohexanecarboxylate (466 mg, 1.19 mmol) in dry tetrahydrofuran (12 mL) was added 1,3-dioxo-1,3-dihydrobenzo[f]isoindole (258 mg, 1.31 mmol), triphenylphosphine (344 mg, 1.31 mmol) and diethylazodicarboxylate (0.21 mL, 1.31 mmol). The resulting mixture was stirred at room temperature for 6 days. The solvent was evaporated under vacuum and the residue was chromatographed on silica gel eluting first methylene chloride and then with 2% ethyl acetate in methylene chloride to afford 1-[1-tert-butoxycarbonyl-3-(1,3-dioxo-1,3-dihydrobenzo[f]isoindol-2-yl)propylamino]cyclohexanecarboxylic acid benzyl ester as a white solid, 530 mg (78%).

Workup

  1. customThe solvent was evaporated under vacuum
  2. customthe residue was chromatographed on silica gel eluting first methylene chloride

Sources & evidence

ORD record
ord-ebd65d7b773c4b0d84b61c7784fae497
Source dataset
uspto-grants-1998_12
Patent number
US05854275

Reaction notes

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