Water → HCID 57524486, compound

HRID 532111Notes

Reaction equation

HRID 532111 reaction equation
C([O:3][C:4]1[CH:5]=[C:6]([C@H:12]([N:18]2[C:26](=[O:27])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][C:24]=3[NH:28][C:29](=[O:31])[CH3:30])[C:19]2=[O:32])[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])C.N[C@H](C(O)=O)C.O>C(Cl)Cl>[OH:3][C:4]1[CH:5]=[C:6]([C@H:12]([N:18]2[C:26](=[O:27])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][C:24]=3[NH:28][C:29](=[O:31])[CH3:30])[C:19]2=[O:32])[CH2:13][S:14]([CH3:17])(=[O:15])=[O:16])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

5

Reactant 3

HCID 962WaterHCID 5950L-AlanineHCID 11561674Apremilast

Product 1

HCID 57524486HCID 57524486, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (S)—N-{2-[1-(3-ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-acetamide (0.55 mmol) in anhydrous CH2Cl2 at room temperature, is added Ala (1.10 mmol). After stirring for 1 hour, water is added. The product is extracted into CH2Cl2 and is dried over Na2SO4. The solvent is removed to give crude (S)—N—{2-[1-(3-hydroxy-4-methoxy-phenyl)-2-methanesulfonyl-ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-acetamide. The product is purified by chromatography or recrystallization.

Workup

  1. extractionThe product is extracted into CH2Cl2
  2. dry with materialis dried over Na2SO4
  3. customThe solvent is removed

Sources & evidence

ORD record
ord-a8b00ef7f16c48bf8e5a9cc26b42a82d
Source dataset
uspto-grants-2014_10
Patent number
US08853175B2

Reaction notes

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