Phthalimide → HCID 67458000, compound

HRID 1713316Notes

Reaction equation

HRID 1713316 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:17]=[C:18]([C:22]2[CH:27]=[CH:26][C:25]([CH2:28]O)=[CH:24][CH:23]=2)[CH:19]=[CH:20][CH:21]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:30]1(=[O:40])[NH:34][C:33](=[O:35])[C:32]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:31]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:17]=[C:18]([C:22]2[CH:23]=[CH:24][C:25]([CH2:28][N:34]3[C:30](=[O:40])[C:31]4=[CH:39][CH:38]=[CH:37][CH:36]=[C:32]4[C:33]3=[O:35])=[CH:26][CH:27]=2)[CH:19]=[CH:20][CH:21]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 67456713HCID 67456713, compound

Product 1

HCID 67458000HCID 67458000, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[3′-(4-Benzyloxycarbonylaminobutyl)biphenyl-4-yl]-methanol (0.40 g) was dissolved in tetrahydrofuran (4.1 mL). After addition of phthalimide (0.14 g) and triphenylphosphine (0.26 g) were added, diisopropyl azodicarboxylate (40% toluene solution, 0.5 g) was added dropwise, and the resulting mixture was stirred at room temperature for 6 hours. The reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=2/1) to give the title compound (0.4 g)

Workup

  1. additionwere added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-cdf9887cd4614cb78783b8e0f580468c
Source dataset
uspto-grants-2010_09
Patent number
US07795236B2

Reaction notes

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