Phthalimide → tert-Butyl [2-phthalimido-1-(methylsulfanylmethyl)ethyl]carbamate

HRID 1504831Notes

Reaction equation

HRID 1504831 reaction equation
O[CH2:2][CH:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:4][S:5][CH3:6].[C:15]1(=[O:25])[NH:19][C:18](=[O:20])[C:17]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:16]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[O:20]=[C:18]1[C:17]2[C:16](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15](=[O:25])[N:19]1[CH2:2][CH:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:4][S:5][CH3:6]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 15192845Tert-butyl [1-hydroxy-3-(methylsulfanyl)propan-2-yl]carbamate

Product 1

HCID 24720892tert-Butyl [2-phthalimido-1-(methylsulfanylmethyl)ethyl]carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl [1-hydroxy-3-(methylsulfanyl)propan-2-yl]carbamate (14.0 g, 63.3 mmol) in THF (200 mL) was added phthalimide (11.2 g, 76.0 mmol) and triphenylphosphine (25.3 g, 94.9 mmol) under a nitrogen atmosphere. Diethylazodicarboxylate was added dropwise and the reaction mixture was stirred at room temperature. After 2 hours, the reaction mixture was concentrated under reduced pressure. The residue was purified via chromatography on silica gel to afford tert-butyl [1-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-(methylsulfanyl)propan-2-yl]carbamate. MS ESI calc'd. for C17H22N2O4SNa [M+Na]+ 373. found 373. 1H NMR (400 MHz, CD3OD) δ 7.85-7.77 (m, 4H), 4.16-4.05 (m, 1H), 3.92-3.68 (m, 2H), 2.69-2.15 (m, 2H), 2.15 (s, 3H), 1.25 (s, 9H).

Workup

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

Sources & evidence

ORD record
ord-4d0b8851d0cd42a18c2c81adb48bb8be
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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