Phthalimide → HCID 131719746, compound

HRID 1080844Notes

Reaction equation

HRID 1080844 reaction equation
CC(C)(OC([N:7]1[CH2:11][CH2:10][CH2:9][C@H:8]1[CH2:12][S:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17][N:18]1[C:26](=[O:27])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]1=[O:28])=O)C.BrC1C=CC2C(NC(=O)C2(C=CCC)C=1)=O.C1(=O)NC(=O)C2=CC=CC=C12.[ClH:57].O1CCOCC1>C(Cl)Cl>[ClH:57].[NH:7]1[CH2:11][CH2:10][CH2:9][C@H:8]1[CH2:12][S:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17][N:18]1[C:26](=[O:27])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]1=[O:28]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 204431481,4-Dioxane hydrochlorideHCID 70061973HCID 70061973, compoundHCID 70069984HCID 70069984, compound

Product 1

HCID 131719746HCID 131719746, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S,Z)-2-[4-[[[1-[(1,1-dimethylethoxy)carbonyl]-2-pyrrolidinyl]methyl]thio]-2-butenyl]-1H-isoindole-1,3(2H) -dione, (prepared as in Example I, Part A, except substituting 4-bromo-2-butenyl phthalimide for the corresponding phthalimide) (3.60 mmol)) in 2 mL of CH2Cl2 was added 18 mL of 4N HCl/dioxane at 0° C. The ice bath was removed and the reaction was stirred at room temperature for 3 hrs. The reaction mixture was concentrated in vacuo to give title compound (92% yield).

Workup

  1. customThe ice bath was removed
  2. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-9b72998ba6084302a183dfa460b85a69
Source dataset
uspto-grants-1996_12
Patent number
US05583146

Reaction notes

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