Phthalimide → HCID 90136018, compound

HRID 2275795Notes

Reaction equation

HRID 2275795 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][CH2:7][CH:8](O)[CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][CH:3]=1.[C:21]1(=[O:31])[NH:25][C:24](=[O:26])[C:23]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:22]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>C1COCC1>[O:26]=[C:24]1[C:23]2[C:22](=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:21](=[O:31])[N:25]1[CH:8]([CH2:7][O:6][C:5]1[CH:19]=[CH:20][C:2]([F:1])=[CH:3][CH:4]=1)[CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 90136001HCID 90136001, compound

Product 1

HCID 90136018HCID 90136018, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At RT, 1.5 g of rac-tert-butyl [3-(4-fluorophenoxy)-2-hydroxypropyl]carbamate (5.26 mmol, 1 equivalent), 0.93 g of phthalimide (6.31 mmol, 1.2 equivalents) and 2.07 g of triphenylphosphine (7.9 mmol, 1.5 equivalents) were initially charged in 22 ml of dry THF. 1.56 ml of diisopropyl azodicarboxylate (7.9 mmol, 1.5 equivalents) were added dropwise, and the mixture was stirred at RT for 2 h. The reaction mixture was concentrated under reduced pressure and purified by chromatography on silica gel (Biotage Isolera; cyclohexane/ethyl acetate gradient as mobile phase). This gave 1.97 g of the title compound (90% of theory).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified by chromatography on silica gel (Biotage Isolera; cyclohexane/ethyl acetate gradient as mobile phase)

Sources & evidence

ORD record
ord-c680c07d9acf49e58e5179058030b395
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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