Triphenylphosphine → HCID 86753502, compound

HRID 1459886Notes

Reaction equation

HRID 1459886 reaction equation
[C:1]([O:5][C:6](=[O:35])[CH:7]([CH2:11][C:12]1([C:18](=[O:34])[NH:19][CH:20]([C:30](=[O:33])[NH:31][CH3:32])[CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[CH2:8][CH2:9]O)([CH3:4])([CH3:3])[CH3:2].[O:36]=[C:37]1[C:45]2[CH:44]=[C:43]3[CH:46]=[CH:47][CH:48]=[CH:49][C:42]3=[CH:41][C:40]=2[C:39](=[O:50])[NH:38]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[C:1]([O:5][C:6](=[O:35])[CH:7]([CH2:11][C:12]1([C:18](=[O:34])[NH:19][CH:20]([C:30](=[O:33])[NH:31][CH3:32])[CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[CH2:8][CH2:9][N:38]1[C:39](=[O:50])[C:40]2[CH:41]=[C:42]3[CH:49]=[CH:48][CH:47]=[CH:46][C:43]3=[CH:44][C:45]=2[C:37]1=[O:36])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 3351942,3-NaphthalenedicarboximideHCID 5462977Diethyl azodicarboxylateHCID 867535004-Hydroxy-2-{1-[2-(4-methoxyphenyl)-1-(methylcarbamoyl)ethylcarbamoyl]cyclohexylmethyl}butyric acid tert-butyl ester

Product 1

HCID 86753502HCID 86753502, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-hydroxy-2-{1-[2-(4-methoxyphenyl)-1-(methylcarbamoyl)-ethylcarbamoyl]cyclohexylmethyl}butyric acid tert-butyl ester (490 mg, 1.0 mmol) in dry tetrahydrofuran (20 mL) was added 1,3-dioxo-1,3-dihydrobenzo[f]isoindole (394 mg, 2.0 mmol), triphenylphosphine (524 mg, 2.0 mmol) and diethylazodicarboxylate (0.31 mL, 2.0 mmol). The resulting mixture was stirred for 3 days. The solvent was evaporated under vacuum and the residue was chromatographed on silica gel eluting with 40% ethyl acetate in hexane. Fractions containing the two diastereomeric products were combined and evaporated to leave a white solid which was recrystallized from ethyl acetate to afford 4-(1,3-dioxo-1,3-dihydrobenzo [f]isoindol-2-yl)-2-{1-[2-(4-methoxyphenyl)-1-(methylcarbamoyl)-ethylcarbamoyl]cyclohexylmethyl}butyric acid tert-butyl ester (diastereomer A) as a white solid, 105 mg (16%). The mother liquor from the recrystallization was concentrated under vacuum to afford an oil highly enriched in diastereomer B, 140 mg (21%).

Workup

  1. customThe solvent was evaporated under vacuum
  2. customthe residue was chromatographed on silica gel eluting with 40% ethyl acetate in hexane
  3. additionFractions containing the two diastereomeric products
  4. customevaporated
  5. customto leave a white solid which
  6. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-241629a6d49c4b78b58eddc847415e98
Source dataset
uspto-grants-1998_12
Patent number
US05854275

Reaction notes

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