Lithium Hydroxide → HCID 10222189, compound

HRID 2120675Notes

Reaction equation

HRID 2120675 reaction equation
C([O:3][C:4](=[O:43])[CH2:5][CH:6]([C:33]1[CH:34]=[N:35][C:36]2[C:41]([CH:42]=1)=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[N:18]=[C:17]([NH:19]C(=O)C(C)(C)C)[N:16]=[C:15]([NH:26]C(=O)C(C)(C)C)[CH:14]=1)C.[Li+].[OH-]>O>[NH2:19][C:17]1[N:16]=[C:15]([NH2:26])[CH:14]=[C:13]([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH:6]([C:33]2[CH:34]=[N:35][C:36]3[C:41]([CH:42]=2)=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:5][C:4]([OH:43])=[O:3])[N:18]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69666423HCID 69666423, compound

Product 1

HCID 10222189HCID 10222189, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The ester 7-8 (1 g, 1.7 mmol) was dissolved in TBF (20 mL) and water (20 mL) and treated with 1N LiOH (7 mL) at room temperature for 16 hours. After neutralization with 3N HCl, the solution was concentrated in vacuo, filtered through a bed of silica gel (EtOH:H2O:NH4OH 10:1:1) and the residue purified by reverse phase HPLC (preppak C-18 column; water/acetonitrile/0.1% TFA gradient). After lyophilization, the title compound 7-9 (TFA salt) was obtained as a white powder.

Workup

  1. concentrationAfter neutralization with 3N HCl, the solution was concentrated in vacuo
  2. filtrationfiltered through a bed of silica gel (EtOH:H2O:NH4OH 10:1:1)
  3. customthe residue purified by reverse phase HPLC (preppak C-18 column; water/acetonitrile/0.1% TFA gradient)

Sources & evidence

ORD record
ord-617a815c87574fdca960ffd11bd9258f
Source dataset
uspto-grants-2004_02
Patent number
US06693101B2

Reaction notes

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