Phthalimide → HCID 86705526, compound

HRID 2279526Notes

Reaction equation

HRID 2279526 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@@H:12](O)[CH2:13][N:14]([CH3:22])[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].[C:24]1(=[O:34])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26](=[O:33])[NH:25]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[O:34]=[C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26](=[O:33])[N:25]1[C@@H:12]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([F:11])([F:10])[F:9])=[C:2]([F:1])[CH:3]=1)[CH2:13][N:14]([CH3:22])[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 86705525HCID 86705525, compound

Product 1

HCID 86705526HCID 86705526, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 262 (0.98 g, 2.91 mmol) and THF (30 mL) cooled to 0° C. was added sequentially isoindoline-1,3-dione (0.470 g, 3.20 mmol) and PPh3 (1.14 g, 4.36 mmol), followed by a solution of DEAD (1.72 mL, 4.36 mmol) and THF (10 mL). The reaction was warmed to RT and stirred overnight. The reaction was concentrated to dryness, Et2O (300 mL) added and the resulting solid was filtered and discarded. The filtrate was then poured into water, and extracted with DCM. The combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with DCM:MeOH (500:2) to afford 0.99 g (73.1%) of (S)-tert-butyl 2-(1,3-dioxoisoindolin-2-yl)-2-(3-fluoro-4-(trifluoromethyl)phenyl)ethyl(methyl)carbamate (264).

Workup

  1. concentrationThe reaction was concentrated to dryness, Et2O (300 mL)
  2. additionadded
  3. filtrationthe resulting solid was filtered
  4. additionThe filtrate was then poured into water
  5. extractionextracted with DCM
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by SiO2 chromatography
  10. washeluting with DCM:MeOH (500:2)

Sources & evidence

ORD record
ord-b7b03a42d6c1475a875161b1138285c1
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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