tert-Butyl carbazate → HCID 66839144, compound

HRID 546705Notes

Reaction equation

HRID 546705 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]([CH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1)[C:30]([OH:32])=O.[C:39]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])(=[O:42])[NH:40][NH2:41]>C(Cl)Cl.O.C(OCC)(=O)C>[Cl:25][CH2:26][CH2:27][CH2:28][CH:29]([CH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1)[C:30]([NH:41][NH:40][C:39]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[O:32]

Participants

8

Reactant 4

HCID 70091tert-Butyl carbazateHCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 66839108HCID 66839108, compound

Product 1

HCID 66839144HCID 66839144, compoundYield 37.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

IPEA (1.03 ml) and BOPCl (756 mg) were added to a solution of the crude 5-chloro-2-(tetrahydropyran-4-yl)valeric acid (442 mg) and tert-butyl carbazate (357 mg) in methylene chloride (7 ml), and the reaction solution was stirred at room temperature overnight. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated. The organic layer was sequentially washed with 1 N hydrochloric acid, water, a saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was triturated with ethyl acetate to obtain 250 mg of the title compound. The property values of the compound are as follows.

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was sequentially washed with 1 N hydrochloric acid, water
  3. dry with materiala saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-fc30beb7762e4fda84043703bb88da19
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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