Lithium Hydroxide → HCID 57987346, compound

HRID 1869762Notes

Reaction equation

HRID 1869762 reaction equation
[Li+].[OH-].C[CH:4]([C@@H:8]1[CH2:13][CH2:12][N:11]([C@@H:14]([C:20]2[CH:25]=[CH:24][C:23]([C:26](=[O:33])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:22][CH:21]=2)[CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[C@H:10]([C:34]2[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][CH:35]=2)[CH2:9]1)[C:5]([O-:7])=[O:6]>O.C1COCC1>[C:26]([C:23]1[CH:22]=[CH:21][C:20]([C@H:14]([N:11]2[CH2:12][CH2:13][C@@H:8]([CH2:4][C:5]([OH:7])=[O:6])[CH2:9][C@H:10]2[C:34]2[CH:39]=[CH:38][C:37]([C:40]([F:42])([F:41])[F:43])=[CH:36][CH:35]=2)[CH2:15][CH2:16][CH:17]([CH3:18])[CH3:19])=[CH:25][CH:24]=1)(=[O:33])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86618001HCID 86618001, compound

Product 1

HCID 57987346HCID 57987346, compoundYield 53.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of LiOH (10 mg, 0.42 mmol) in water (0.5 ml) was added to a stirred solution of the ester (Step 3, 42 mg, 0.074 mmol) in THF (1 ml) at RT. The reaction was stirred at RT O/N then quenched with 2N HCl (1 ml). The mixture was partitioned between EtOAc and H2O. The aqueous layer was extracted with EtOAc (×2). The combined extracts were washed with brine (×1), dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography (silica, 2-8% MeOH/DCM) to give the acid (22 mg) as a colourless solid. 1H NMR (400 MHz, CD3OD): δ 0.60-0.70 (1H, m), 0.82-1.02 (7H, m), 1.14-1.24 (1H, m), 1.38-1.49 (2H, m), 1.72-1.75 (1H, m), 1.84-1.95 (4H, m), 2.18-2.20 (2H, m), 2.52 (1H, brt, J 11), 2.82 (1H, brd, J 11), 3.53 (1H, dd, J 9.8, 4.0), 3.87 (1H, brd, J 10), 7.45 (2H, d, J 8.2), 7.52 (2H, t, J 7.6), 7.64 (1H, J 7.4), 7.70-7.80 (8H, m); M/Z (ES+) 552 (MH+).

Workup

  1. customthen quenched with 2N HCl (1 ml)
  2. customThe mixture was partitioned between EtOAc and H2O
  3. extractionThe aqueous layer was extracted with EtOAc (×2)
  4. washThe combined extracts were washed with brine (×1)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by chromatography (silica, 2-8% MeOH/DCM)

Sources & evidence

ORD record
ord-54d1a37911654cde95fb7bd83784b4cb
Source dataset
uspto-grants-2009_12
Patent number
US07638629B2

Reaction notes

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