tert-Butyl carbazate → HCID 66618881, compound

HRID 406328Notes

Reaction equation

HRID 406328 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH:5]([C:9]1[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[C:12]([O:18][CH3:19])=[CH:11][C:10]=1[CH3:20])[C:6]([OH:8])=O.[C:21]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])(=[O:24])[NH:22][NH2:23].C(N(CC)C(C)C)(C)C.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1>ClCCl>[Cl:1][CH2:2][CH2:3][CH2:4][CH:5]([C:9]1[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[C:12]([O:18][CH3:19])=[CH:11][C:10]=1[CH3:20])[C:6]([NH:23][NH:22][C:21]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:8]

Participants

6

Reactant 4

HCID 70091tert-Butyl carbazateHCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 66618720HCID 66618720, compound

Product 1

HCID 66618881HCID 66618881, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Chloro-2-(5-isopropyl-4-methoxy-2-methylphenyl)pentanoic acid (6.2 g), tert-butyl carbazate (4.1 g) and N,N-diisopropylethylamine (10.8 mL) were dissolved in dichloromethane (120 mL). Bis(2-oxo-3-oxazolidinyl)phosphinic acid chloride (7.9 g) was added under ice-cooling. After addition of the reagent, the mixture was brought back to room temperature and stirred overnight. The reaction solution was concentrated under reduced pressure. A sodium bicarbonate solution and tert-butyl methyl ether were added and the organic layer was separated. The resulting organic layer was washed with brine and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration, and then the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (6.1 g). The property values of the compound are as follows.

Workup

  1. temperaturecooling
  2. additionAfter addition of the reagent
  3. customwas brought back to room temperature
  4. concentrationThe reaction solution was concentrated under reduced pressure
  5. additionA sodium bicarbonate solution and tert-butyl methyl ether were added
  6. customthe organic layer was separated
  7. washThe resulting organic layer was washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe drying agent was separated by filtration
  10. concentrationthe organic layer was concentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-879b630bbd0f4019bfa97051b7e7e305
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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