Phthalimide → tert-butyl [1-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-(methylsulfanyl)butan-2-yl]carbamate

HRID 1504839Notes

Reaction equation

HRID 1504839 reaction equation
O[CH2:2][CH:3]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:5][S:6][CH3:7].[C:16]1(=[O:26])[NH:20][C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[O:21]=[C:19]1[C:18]2[C:17](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16](=[O:26])[N:20]1[CH2:2][CH:3]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:5][S:6][CH3:7]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 11356792Tert-butyl [1-hydroxy-4-(methylsulfanyl)butan-2-yl]carbamate

Product 1

HCID 86731711tert-butyl [1-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-(methylsulfanyl)butan-2-yl]carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl [1-hydroxy-4-(methylsulfanyl)butan-2-yl]carbamate (18.5 g, 84.5 mmol) in THF (400 mL) was added phthalimide (14.9 g, 0.101 mol) and triphenylphosphine (26.9 g, 0.101 mol) under a nitrogen atmosphere. Diethylazodicarboxylate (27.3 g, 0.135 mol) was added dropwise at room temperature. After 2 hours, the reaction mixture was concentrated under reduced pressure, and the residue was purified by chromatography on silica gel to give tert-butyl {1-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-(methylsulfanyl)butan-2-yl}carbamate. MS ESI calc'd. for C18H25N2O4S [M+H]+ 365. found 365. 1H NMR (400 MHz, CDCl3) δ 7.87-7.71 (m, 4H), 4.72 (s, 1H), 4.16-4.07 (m, 1H), 3.76 (d, J=6.6 Hz, 2H), 2.68-2.54 (m, 2H), 2.13 (s, 3H), 1.75-1.55 (m, 2H), 1.35 (s, 9H).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-74acde5b2fd44b5ebde356818d5c64c3
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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