Phthalamide → 2-[2-(Tritylsulfanyl)benzyl]-1H-isoindole-1,3(2H)-dione

HRID 2096245Notes

Reaction equation

HRID 2096245 reaction equation
[C:1]([S:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27]O)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29]([NH2:40])(=[O:39])[C:30]1[C:31](=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:32](N)=[O:33].S1C=CC=C1P.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([S:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][N:40]1[C:29](=[O:39])[C:30]2[C:31](=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:32]1=[O:33])([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6956PhthalamideHCID 5462977Diethyl azodicarboxylateHCID 21095809ThienylphosphineHCID 66822213(2-Tritylsulfanylphenyl)-methanol

Product 1

HCID 668222702-[2-(Tritylsulfanyl)benzyl]-1H-isoindole-1,3(2H)-dioneYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-tritylsulfanylphenyl)-methanol (4.7 g, 12.3 mmol), phthalamide (2.29 g, 15.6 mmol) and thiphenylphosphine (4.09 g, 15.6 mmol) in THF (70 mL) at 0° C. under an argon atmosphere, was slowly added DEAD (2.4 mL, 15 mmol). The reaction mixture was stirred at RT for 30 min, then partitioned between aqueous saturated NaHCO3 and EtOAc. The organic layer was separated, dried over MgSO4, filtered, and the filtrate was concentrated in vacuo to afford the title compound (4.7 g, 75%) as yellow foam. 1H NMR (300 MHz, CDCl3): δ 7.82 (2H, m), 7.70 (2H, m), 7.38-7.33 (5H, m), 7.27-7.22 (10H, m), 7.12 (1H, dd, J 1.4, 0.5), 7.08 (1H, dt, J 1.4, 0.5), 6.96 (1H, dd, J 7.6, 1.5), 6.88 (1H, dt, J 7.6, 1.5), 4.47 (2H, s).

Workup

  1. customat 0° C.
  2. custompartitioned between aqueous saturated NaHCO3 and EtOAc
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-09d9b9c9c4854bf197bd04515e1231ee
Source dataset
uspto-grants-2013_05
Patent number
US08450314B2

Reaction notes

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