Sodium Hydroxide → HCID 59664692, compound

HRID 2422384Notes

Reaction equation

HRID 2422384 reaction equation
[CH3:1][O:2][CH:3]([CH2:8][C:9]1[N:10]=[CH:11][N:12]([C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=1)[C:4]([O:6]C)=[O:5].[OH-].[Na+]>O1CCCC1.CO.O>[CH3:1][O:2][CH:3]([CH2:8][C:9]1[N:10]=[CH:11][N:12]([C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=1)[C:4]([OH:6])=[O:5]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 59664693HCID 59664693, compound

Product 1

HCID 59664692HCID 59664692, compoundYield 96.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-methoxy-3-(1-trityl-1H-imidazol-4-yl)propanoate (0.0592 g, 0.139 mmol) in tetrahydrofuran (1 mL), methanol (1 mL) and water (0.5 mL) was added 2N NaOH (0.278 mL) and the reaction mixture was stirred for 1.75 hrs. The organic solvents were removed and 1 N KHSO4 (5 mL) and ethyl acetate (10 mL) were added. The organic phase was washed with water (2×5 mL), then saturated sodium chloride (1×5 mL) and dried over MgSO4. The combined aqueous layers were re-extracted with DCM (2×10 mL), and dried over MgSO4—Solvent removal and drying in vacuo yielded 0.0552 g (96%) of 92.6% pure 2-methoxy-3-(1-trityl-1H-imidazol-4-yl)propanoic acid; retention time, 6.80 min.; column: Phenomenex Luna C18(2) (5 μm, 50×4.6 mm); gradient: 10% to 100% B in A over 10 min. at 1.25 mL/min. Solvent A: 0.1% TFA in water, Solvent B: 0.1% TFA in AcCN. LC/MS: ESI (M+H)+=413.1. 1H-NMR (CDCl3, 500 MHz): δ 3.10-3.18 (m, 1H), 3.31-3.38 (m, 1H), 3.45 (s, 3H), 4.26-4.31 (m (1H), 6.86 (s, 1H), 7.04-7.11 (m, 6H), 7.37-7.47 (m, 9H), 8.16 (s, 1H).

Workup

  1. customThe organic solvents were removed
  2. addition1 N KHSO4 (5 mL) and ethyl acetate (10 mL) were added
  3. washThe organic phase was washed with water (2×5 mL)
  4. dry with materialsaturated sodium chloride (1×5 mL) and dried over MgSO4
  5. extractionThe combined aqueous layers were re-extracted with DCM (2×10 mL)
  6. dry with materialdried over MgSO4—Solvent removal
  7. customdrying in vacuo

Sources & evidence

ORD record
ord-6c6804ba6c3f4bbfaca4d0fc11a6ec82
Source dataset
uspto-grants-2011_06
Patent number
US07960349B2

Reaction notes

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