Hydrochloric Acid → HCID 67067393, compound

HRID 1009378Notes

Reaction equation

HRID 1009378 reaction equation
C(N(C(C)C)CC)(C)C.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.[Cl:25][CH2:26][CH2:27][CH2:28][CH:29]([C:33]1[C:38]([F:39])=[CH:37][C:36]([F:40])=[CH:35][C:34]=1[F:41])[C:30]([OH:32])=O.[C:42]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])(=[O:45])[NH:43][NH2:44].Cl>C(Cl)Cl.C(OCC)(=O)C>[Cl:25][CH2:26][CH2:27][CH2:28][CH:29]([C:33]1[C:38]([F:39])=[CH:37][C:36]([F:40])=[CH:35][C:34]=1[F:41])[C:30]([NH:44][NH:43][C:42]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])=[O:32]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 70091tert-Butyl carbazateHCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 67067436HCID 67067436, compound

Product 1

HCID 67067393HCID 67067393, compoundYield 41.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

IPEA (1.1 mL) and BOPCl (798 mg) were added to a solution of 5-chloro-2-(2,4,6-trifluorophenyl)pentanoic acid (560 mg) synthesized according to the method described in Tetrahedron Letters, 2003, vol. 44, p. 365 and tert-butyl carbazate (276 mg) in methylene chloride (5 mL), and the reaction solution was stirred at room temperature for one hour. Ethyl acetate and 1 N aqueous hydrochloric acid were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with saturated sodium bicarbonate water, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane->heptane:ethyl acetate=1:1) to obtain 333 mg of the title compound. The property values of the compound are as follows.

Workup

  1. customsynthesized
  2. customthe organic layer was separated
  3. washThe resulting organic layer was washed with saturated sodium bicarbonate water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (elution solvent: heptane->heptane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-5b661bed21924c128725b0cd7779c81e
Source dataset
uspto-grants-2011_07
Patent number
US07973033B2

Reaction notes

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