Hydrochloric Acid → HCID 131736479, compound

HRID 1477086Notes

Reaction equation

HRID 1477086 reaction equation
[CH3:1][NH:2][C:3](=[O:15])[O:4][CH2:5][C@H:6]([NH2:14])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CS(O)(=O)=O.[O-:21][C:22]#[N:23].[Na+].[OH-].[Na+].Cl>ClCCl.C(OCC)C.O>[NH2:23][C:22]([CH2:1][NH:2][C:3](=[O:15])[O:4][CH2:5][C@H:6]([NH2:14])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:21]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 517096Sodium CyanateHCID 10176662HCID 10176662, compound

Product 1

HCID 131736479HCID 131736479, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

(2R)-2-amino-3-phenylpropyl methylcarbamate (11.932 mmol) was dissolved in dichloromethane and methansulfonic acid (3.1 ml, 4 eq) and sodium cyanate (5.39 g, 3 eq) was added in an ice bath. The resulting reaction mixture was stirred for 1 day. Water was added to terminate the reaction and the reaction mixture was basicified to pH8-9 with 1N NaOH solution. The organic layer was extracted 3 times with dichloromethane, dried over magnesium sulfate and concentrated in vacuo, to give oil. This was dissolved in dichloromethane and the solution was treated with a solution of HCl in ethyl ether. The resulting precipitate was filtered to give (2R)-2-amino-3-phenylpropyl (aminocarbonyl)methylcarbamate; hydrochloride

Workup

  1. customThe resulting reaction mixture
  2. customto terminate
  3. customthe reaction
  4. extractionThe organic layer was extracted 3 times with dichloromethane
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give oil
  8. filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record
ord-8d4a8e78ecf440488eb9ed69d3f6f5cc
Source dataset
uspto-grants-2016_08
Patent number
US09403761B2

Reaction notes

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