Lithium Hydroxide → HCID 58573785, compound

HRID 1048358Notes

Reaction equation

HRID 1048358 reaction equation
[N:1]([C@H:4]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][N:20]=1)[C@@H:5]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=1)[CH2:6][CH2:7][C:8](OC)=[O:9])=[N+]=[N-].CP(C)C.[Li+].[OH-]>C1COCC1.O>[Cl:18][C:14]1[CH:13]=[C:12]([C@@H:5]2[C@@H:4]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][N:20]=3)[NH:1][C:8](=[O:9])[CH2:7][CH2:6]2)[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 68983TrimethylphosphineHCID 58573733HCID 58573733, compound

Product 1

HCID 58573785HCID 58573785, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Crude (4R,5S)-methyl 5-azido-4-(3-chlorophenyl)-5-(5-chloropyridin-2-yl)pentanoate (463 g, 1.22 mol, Example 121, Step E) was dissolved in 2.5 L THF/water (4:1). Trimethyl phosphine (1 M in THF, 1.46 L, 1.46 mol, 1.2 eq) was added slowly at 0-5° C. The reaction was stirred for 30 min and then basified with 2.0 M aqueous LiOH solution to pH 12. The reaction mixture was stirred for another 30 min, and extracted to ethyl acetate (2×5 L). The combined organic layers were washed with sat. NaCl solution, dried over Na2SO4, filtered and the filtrate was concentrated under reduced pressure.

Workup

  1. stirringThe reaction mixture was stirred for another 30 min
  2. extractionextracted to ethyl acetate (2×5 L)
  3. washThe combined organic layers were washed with sat. NaCl solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-88b630d4ff624e2bac36b20ceacc7b00
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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