Water → HCID 10222189, compound

HRID 860064Notes

Reaction equation

HRID 860064 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.O.[Li+].[OH-]>C1COCC1>[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

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 69666423HCID 69666423, compound

Product 1

HCID 10222189HCID 10222189, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The ester 7-8 (1 g, 1.7 mmol) was dissolved in THF (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-bd16eadba2f84971b1191a40f4f1c78c
Source dataset
uspto-grants-2006_12
Patent number
US07153862B2

Reaction notes

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