Lithium Hydroxide → HCID 58573785, compound

HRID 932047Notes

Reaction equation

HRID 932047 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-0fe4f3d2ff214bb8a65290b0a6810820
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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