Lithium Hydroxide → HCID 12017184, compound

HRID 2185973Notes

Reaction equation

HRID 2185973 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[O:16][CH2:17][C@@H:18]([C:20]([O:22]CC2C=CC=CC=2)=[O:21])[N:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-]>C1COCC1.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[O:16][CH2:17][C@@H:18]([C:20]([OH:22])=[O:21])[N:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 10178272HCID 10178272, compound

Product 1

HCID 12017184HCID 12017184, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a mixture of benzyl ester (1) (25.7 mg, 0.0664 mmol) in 1:1 THF/H2O (3 mL) at 0° C. was added LiOH (9 mg, 0.348 mmol, 1.5 equiv.). The reaction mixture was stirred for 1 h at room temperature. The desired product 3 was obtained in 99% yield after purification by column chromatography (CH2Cl2/MeOH=85:15). FABMS: 298 (M+1); HREIMS calcd. for C17H15NO4 298.1079, found 298.1078.

Sources & evidence

ORD record
ord-a56daef483d249a887cd42c0377adcec
Source dataset
uspto-grants-2002_06
Patent number
US06403623B1

Reaction notes

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