Phthalimide → HCID 68267473, compound

HRID 1027576Notes

Reaction equation

HRID 1027576 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:31]([N:33]1[CH2:37][CH:36]([CH2:38]O)[CH2:35][S:34]1(=[O:41])=[O:40])[CH3:32].CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[CH2:31]([N:33]1[CH2:37][CH:36]([CH2:38][N:5]2[C:1](=[O:11])[C:2]3[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4]2=[O:6])[CH2:35][S:34]1(=[O:41])=[O:40])[CH3:32]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 68267476HCID 68267476, compound

Product 1

HCID 68267473HCID 68267473, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of phthalimide (133 mg, 1 equiv) in tetrahydrofuran (4.5 ml) was added triphenylphosphine (237 mg, 1 equiv) and (2-Ethyl-1,1-dioxo-1lambda*6*-isothiazolidin-4-yl)-methanol (0.905 mmol). This solution was cooled down to 0° C. for the dropwise addition of diisopropylazodicarboxylate (0.18 ml, 1 equiv). The reaction mixture was stirred at room temperature over the weekend. It was then concentrated, and stirred in diethyl ether for 5 hours. Volatiles were removed in vacuo. Flash chromatography eluting with cyclohexane/ethyl acetate (7/3) afforded 261 mg (0.85 mmol, 94%). LCMS (Method E) 1.40 min, M+H 309. 1H-NMR (CDCl3, 400 MHz): 7.93-7.84 (m, 2H), 7.83-7.72 (m, 2H), 3.89 (dd, 2H), 3.41-3.23 (m, 2H), 3.17-2.98 (m, 5H), 1.22 (t, 3H).

Workup

  1. concentrationIt was then concentrated
  2. stirringstirred in diethyl ether for 5 hours
  3. customVolatiles were removed in vacuo
  4. washFlash chromatography eluting with cyclohexane/ethyl acetate (7/3)
  5. customafforded 261 mg (0.85 mmol, 94%)
  6. customLCMS (Method E) 1.40 min, M+H 309

Sources & evidence

ORD record
ord-1722bfc84c904347a164ea94a1cab99f
Source dataset
uspto-grants-2014_05
Patent number
US08735362B2

Reaction notes

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