Phthalimide → HCID 20601400, compound

HRID 480084Notes

Reaction equation

HRID 480084 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17]O)=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)=[O:4].[C:19]1(=[O:29])[NH:23][C:22](=[O:24])[C:21]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1.C(OCC)C.O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]2[CH:12]=[CH:13][C:14]([CH2:17][N:23]3[C:19](=[O:29])[C:20]4[C:21](=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:22]3=[O:24])=[CH:15][CH:16]=2)[CH:8]=[CH:9][CH:10]=1)=[O:4]

Participants

8

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 20100116Methyl 4'-(hydroxymethyl)[1,1'-biphenyl]-3-carboxylate

Product 1

HCID 20601400HCID 20601400, compoundYield 139.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 1.4 g (5.8 mmol.) 4′-hydroxymethyl-biphenyl-3-carboxylic acid methyl ester, 1.0 g (6.9 mmol.) phthalimide and 1.8 g (6.9 mmol.) triphenylphosphine in 25 mL tetrahydrofuran at 0° C. was added 1.2 ml (7.5 mmol.) diethylazodicarboxylate. The mixture was warmed to ambient temperature and stirred for 18 hours. The mixture was poured into water and extracted with ethyl acetate. The ethyl acetate extracts were combined then washed successively with 1N NaOH, 1N HCl, water, brine then dried (MgSO4) and concentrated in vacuo to give a solid. Trituration with diethyl ether gave 3.0 g 4′-[1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl]-biphenyl-3-carboxylic acid methyl ester as a solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate extracts were combined then washed successively with 1N NaOH, 1N HCl, water, brine
  3. dry with materialthen dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto give a solid

Sources & evidence

ORD record
ord-fa812fe3a8d94180b8f291bdc1d11e34
Source dataset
uspto-grants-2003_11
Patent number
US06649633B2

Reaction notes

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