Hydrochloric Acid → HCID 118351629, compound

HRID 1477087Notes

Reaction equation

HRID 1477087 reaction equation
[C:1](=[O:14])([O:3][CH2:4][C@H:5]([NH2:13])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH2:2].CS(O)(=O)=O.[C:20]1([N:26]=[C:27]=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[OH-].[Na+].Cl>ClCCl.C(OCC)C.O>[NH:26]([C:27]([NH:2][C:1](=[O:14])[O:3][CH2:4][C@H:5]([NH2:13])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6395Methanesulfonic AcidHCID 7672Phenyl isocyanateHCID 14798Sodium HydroxideHCID 10130337Solriamfetol

Product 1

HCID 118351629HCID 118351629, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

(2R)-2-amino-3-phenylpropyl carbamate (2.397 mmol) was dissolved in dichloromethane and methansulfonic acid (0.47 ml, 3 eq) and phenyl isocyanate (1.56 ml, 6 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 neutralized to pH 7-8 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 (anilinocarbonyl)carbamate; 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-a7836ffa7e7c4441a4232d7e5809a764
Source dataset
uspto-grants-2016_08
Patent number
US09403761B2

Reaction notes

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