Lithium hydroxide, monohydrate → HCID 86627966, compound

HRID 251742Notes

Reaction equation

HRID 251742 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].CO[C:10]([NH:12][C@H:13]([C:23]1[NH2+:24][C:25]([C:28]2[CH:37]=[CH:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:29]=2)=[CH:26][N:27]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19](=[O:22])[CH2:20][CH3:21])=[O:11].O[Li].[OH2:40]>C1COCC1.O>[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[C:3]([C:10]([NH:12][C@H:13]([C:23]1[NH2+:24][C:25]([C:28]2[CH:37]=[CH:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:29]=2)=[CH:26][N:27]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19](=[O:22])[CH2:20][CH3:21])=[O:11])([OH:4])=[O:40]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86627967HCID 86627967, compound

Product 1

HCID 86627966HCID 86627966, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl ({(1S)-1-[5-(2-naphthyl)-1H-imidazol-2-yl]-7-oxononyl}amino)(oxo)acetate (Prepared as in example 147) was dissolved in THF and a solution of LiOH.H2O (1.05 eq.) in H2O was added and the mixture was then stirred for 1 hr at RT. The reaction was quenched with 1M HCl until pH 5 was reached and then the THF was removed under reduced pressure. The aqueous phase was extracted with DCM (3×); the combined organic phases were washed with brine and then dried (Na2SO4) and concentrated under reduced pressure. The resulting crude was purified by preparative RP-HPLC, using H2O (0.1% TFA) and MeCN (+0.1% TFA) as eluents (column: C18). The desired fractions were lyophilized to afford the titled compound as colorless oil. 1H NMR (300 MHz, DMSO-d6) δ: 9.39 (1H, d, J=8.2 Hz), 8.30 (1H, s), 8.11-7.85 (6H, m), 7.58-7.47 (2H, m), 6.88-6.18 (1H, bs), 5.15-5.02 (1H, m), 2.45-2.36 (4H, m), 2.13-1.87 (2H, m), 1.55-1.41 (2H, m), 1.40-1.20 (4H, m), 0.90 (3H, t, J=7.3 Hz). MS (ES) C24H27N3O4 requires: 421, found: 422 (M+H)+.

Workup

  1. customThe reaction was quenched with 1M HCl until pH 5
  2. customthe THF was removed under reduced pressure
  3. extractionThe aqueous phase was extracted with DCM (3×)
  4. washthe combined organic phases were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting crude was purified by preparative RP-HPLC

Sources & evidence

ORD record
ord-dba3f41bec1b4113bb35a99662bcb967
Source dataset
uspto-grants-2011_01
Patent number
US07863294B2

Reaction notes

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