Lithium Hydroxide → HCID 9884766, compound

HRID 1276384Notes

Reaction equation

HRID 1276384 reaction equation
C[O:2][C:3](=[O:27])[C@H:4]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[NH:5][C:6]1[C:9](=[O:10])[C:8](=[O:11])[C:7]=1[NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Li+].[OH-]>C1COCC1>[CH2:13]([NH:12][C:7]1[C:8](=[O:11])[C:9](=[O:10])[C:6]=1[NH:5][C@H:4]([C:3]([OH:27])=[O:2])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 15479332HCID 15479332, compound

Product 1

HCID 9884766HCID 9884766, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of [2-(benzylamino)-3,4-dioxo-cyclobut-1-enyl]-L-phenylalanine methyl ester (0.16 mmol, 60 mg) in THF (5 mL) was added aqueous LiOH (1.0 M; 0.16 mmol; 160 μL) and the resulting solution was stirred at room temperature for 3 hours. The volatiles were removed in vacuo and the residue partitoned between 0.1M acetic acid and EtOAc. The organics were dried (Na2SO4) and concentrated in vacuo to afford the title compound as a white solid, mp=215-216° C. (33 mg; 59%).

Workup

  1. customThe volatiles were removed in vacuo
  2. dry with materialThe organics were dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-faa6c9fe0d8e4cf093ba91a2940eb3a4
Source dataset
uspto-grants-2000_12
Patent number
US06166050

Reaction notes

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