Hydride → HCID 86588220, compound

HRID 1814327Notes

Reaction equation

HRID 1814327 reaction equation
[C:1]([O:5][C:6](=[O:43])[CH2:7][C@H:8]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:21][C:20]=1[O:30][CH2:31][CH2:32][C:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:36]=[CH:35][CH:34]=1)(=[O:18])=[O:17])[C:9](N(OC)C)=[O:10])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].[H-].S([O-])(O)(=O)=O.[K+]>C1COCC1.CCOCC.O.CCOCC>[C:1]([O:5][C:6](=[O:43])[CH2:7][C@H:8]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:26][CH2:27][CH2:28][CH2:29]2)=[CH:21][C:20]=1[O:30][CH2:31][CH2:32][C:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:36]=[CH:35][CH:34]=1)(=[O:18])=[O:17])[CH:9]=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 166653HydrideHCID 516920Potassium bisulfateHCID 21226445Aluminium lithium hydrideHCID 86588221HCID 86588221, compound

Product 1

HCID 86588220HCID 86588220, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 21868444Ether tetrahydrofuranSolvent

Procedure

To (S)-N-methoxy-N-methyl-3-[2-(2-naphthalen-1-yl-ethoxy)-4-pyrrolidin-1-yl-benzenesulfonylamino]-succinamic acid tert-butyl ester (1.0 g, 1.60 mmol) solution in dry THF/Et2O (2:1, 30 mL) at −65° C. was added LiAlH4 (6.50 mL, 6.5 mmol, 1.0 M solution in Et2O). The reaction mixture temperature was maintained for 2 h. The excess hydride was quenched by the addition of potassium hydrogen sulfate (2 equiv) dissolved in water. After warming to room temperature, Et2O was added (100 mL) and the organic layer was washed with water and then with brine. The solvent was dried (MgSO4), filtered, and evaporated to dryness. The resulting crude product was purified on silica gel flash chromatography (25% EtOAc in hexanes) to give (S)-3-[2-(2-naphthalen-1-yl-ethoxy)-4-pyrrolidin-1-yl-benzenesulfonyl amino]-4-oxo-butyric acid tert-butyl ester as a off white foam (0.60 g, 68%). MS (APCI) m/z 551.3 (M−1).

Workup

  1. temperatureThe reaction mixture temperature was maintained for 2 h
  2. washthe organic layer was washed with water
  3. dry with materialThe solvent was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe resulting crude product was purified on silica gel flash chromatography (25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-ec594b61088541e4bffa74cca6ee2df4
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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