Phosphate → HCID 67148610, compound

HRID 2428158Notes

Reaction equation

HRID 2428158 reaction equation
P(C)(C)C.[C:5]([O:9][C:10](=[O:28])[N:11]([CH2:15][C:16]1[CH:21]=[C:20]([CH2:22][CH2:23][N:24]=[N+]=[N-])[CH:19]=[CH:18][C:17]=1[Cl:27])[CH:12]1[CH2:14][CH2:13]1)([CH3:8])([CH3:7])[CH3:6].P([O-])([O-])([O-])=O>C1COCC1>[C:5]([O:9][C:10](=[O:28])[N:11]([CH2:15][C:16]1[CH:21]=[C:20]([CH2:22][CH2:23][NH2:24])[CH:19]=[CH:18][C:17]=1[Cl:27])[CH:12]1[CH2:13][CH2:14]1)([CH3:8])([CH3:6])[CH3:7]

Participants

5

Reactant 3

HCID 1061PhosphateHCID 68983TrimethylphosphineHCID 86632371HCID 86632371, compound

Product 1

HCID 67148610HCID 67148610, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Me3P (1M in toluene, 4.20 mL, 4.20 mmol) was added to a sol. of [5-(2-azido-ethyl)-2-chloro-benzyl]-cyclopropyl-carbamic acid tert-butyl ester (1.49 g, 4.25 mmol) in THF (13.0 mL), and the mixture was stirred at rt for 5 h. Phosphate buffer (pH 7.4, DPBS Gibco 14200, diluted 10×) was added, and the mixture was extracted with CH2Cl2 several times. The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Drying the residue under high vacuum yielded the crude title compound (1.34 g, 97%) that was used further without purification. LC-MS: tR=0.81 min; ES+: 325.18.

Workup

  1. extractionthe mixture was extracted with CH2Cl2 several times
  2. dry with materialextracts were dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customDrying the residue under high vacuum

Sources & evidence

ORD record
ord-a7f08d6885614e54a818ef08e2116880
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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