Lithium hydroxide, monohydrate → HCID 10143498, compound

HRID 895898Notes

Reaction equation

HRID 895898 reaction equation
C[O:2][C:3](=[O:39])[C@H:4]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:25](=[O:38])[N:26]([CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:27]=[C:28]([Cl:30])[CH:29]=2)=[CH:20][CH:19]=1)[NH:5][C:6]([C:8]1([CH2:13][CH2:14][O:15][CH3:16])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7].O.[OH-].[Li+]>C1COCC1.O.C(O)(=O)C>[Cl:30][C:28]1[CH:29]=[C:24]([C:21]2[CH:20]=[CH:19][C:18]([CH2:17][C@@H:4]([C:3]([OH:39])=[O:2])[NH:5][C:6]([C:8]3([CH2:13][CH2:14][O:15][CH3:16])[CH2:12][CH2:11][CH2:10][CH2:9]3)=[O:7])=[CH:23][CH:22]=2)[C:25](=[O:38])[N:26]([CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:27]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 69716045HCID 69716045, compound

Product 1

HCID 10143498HCID 10143498, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-(1-benzyl-5-chloro-2-oxo-3-pyridinyl)-N-[[1-(2-methoxyethyl)cyclopentyl]carbonyl]-L-phenylalanine methyl ester (78 mg, 0.142 mmol) in THF (3 mL) was treated with a solution of lithium hydroxide monohydrate (24 mg, 0.57 mmol) in water (1.0 mL). Sufficient THF was added to the mixture to effect solution. The mixture was stirred 1 hr and a few drops of acetic acid were added. The entire reaction mixture was applied to a 4×30 cm, C-18 reversed phase HPLC column and eluted with a gradient of acetonitrile in water of 5- to 95% over 35 min. The product containing fraction was lyophillyzed to give 4-(5-chloro-1-benzyl-2-oxo-3-pyridinyl)-N-[[1-(2-methoxyethyl)cyclopentyl]carbonyl]-L-phenylalanine (45 mg, 60%) as a white solid. LRMS-Electrospray: m/z positive ion 559 (M+Na), 554 (M+NH4), 537 (M+H (1 Cl)); negative ion 535 (M−H (1 Cl)). HRMS: obs. mass 537.2151. calcd. mass 537.2156 (M+H).

Workup

  1. customThe entire reaction mixture
  2. washeluted with a gradient of acetonitrile in water of 5- to 95% over 35 min
  3. additionThe product containing fraction

Sources & evidence

ORD record
ord-f16926ea78aa4f809ab732b5a2ff2a3a
Source dataset
uspto-grants-2005_07
Patent number
US06916933B2

Reaction notes

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