Phthalimide → HCID 86655007, compound

HRID 2066844Notes

Reaction equation

HRID 2066844 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][N:14]=[C:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[C:25]([F:27])[C:24]([CH2:28]O)=[CH:23][C:22]=3[F:30])[CH2:17][CH2:16]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(=O)[NH:54]C(=O)C2=CC=CC=C12.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH:1]([O:4][C:5]([N:7]1[CH2:8][CH2:9][CH:10]([O:13][N:14]=[C:15]2[CH2:16][CH2:17][N:18]([C:21]3[CH:26]=[C:25]([F:27])[C:24]([CH2:28][NH2:54])=[CH:23][C:22]=3[F:30])[CH2:19][CH2:20]2)[CH2:11][CH2:12]1)=[O:6])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 58333373HCID 58333373, compound

Product 1

HCID 86655007HCID 86655007, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 10-1 (30 mg, 0.07 mmol), triphenylphosphine (19 mg), phthalimide (11 mg) and DEAD (12 μL) in THF (1 mL) was stirred at room temperature for 3 days. The mixture was concentrated under a stream of nitrogen and combined with DCM (0.2 mL), ethanol (0.5 mL) and hydrazine (50 μL). The mixture was stirred at room temperature for 20 h, filtered and concentrated under a stream of nitrogen. The crude mixture was taken up with methanol and purified by preparative HPLC to afford 16a as a brown oil: LC-MS 408.2 (MH+-17).

Workup

  1. concentrationThe mixture was concentrated under a stream of nitrogen
  2. stirringThe mixture was stirred at room temperature for 20 h
  3. filtrationfiltered
  4. concentrationconcentrated under a stream of nitrogen
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-6f74ff6d1a4f456b8954b7815b82970e
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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