Methanesulfonamide → HCID 67154090, compound

HRID 238919Notes

Reaction equation

HRID 238919 reaction equation
[CH2:1]([O:8][C:9](=[O:31])[C@@H:10]([NH:25][C@H:26]([C:28](O)=[O:29])[CH3:27])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.[CH3:44][S:45]([NH2:48])(=[O:47])=[O:46]>C(Cl)Cl.C([O-])(O)=O.[Na+].CCOC(C)=O>[CH2:1]([O:8][C:9](=[O:31])[C@@H:10]([NH:25][C@@H:26]([CH3:27])[C:28]([NH:48][S:45]([CH3:44])(=[O:47])=[O:46])=[O:29])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 72879MethanesulfonamideHCID 94429TriphosgeneHCID 58280539HCID 58280539, compound

Product 1

HCID 67154090HCID 67154090, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of (S)-2-((S)-1-carboxy-ethylamino)-3-(3′-chloro-biphenyl-4-yl)-propionic acid benzyl ester (600 mg, 1.37 mmol) in DCM (7 mL) and saturated aqueous NaHCO3 solution (2mL) was added triphosgene (407 mg, 1.37 mmol). After being stirred for 0.5 hours, the reaction mixture was diluted with EtOAc and stirred for additional 0.5 hours until generation of gas was completed. The organic layer was separated, washed with brine and concentrated. This was dissolved in DCM (7 mL) and methanesulfonamide (195 mg, 2.06 mmol) was added. After being stirred at rt for 1 hour, the reaction mixture was diluted with EtOAc and washed with brine. The organic layer was dried over Na2SO4, concentrated and purified by silica gel column chromatography (eluent: 10% MeOH in DCM) to give (S)-3-(3′-chloro-biphenyl-4-yl)-2-((S)-2-methanesulfonylamino-1-methyl-2-oxo-ethylamino)-propionic acid benzyl ester. MS: m/z (MH+) 515; HPLC retention time 1.58 min (HPLC condition A).

Workup

  1. stirringstirred for additional 0.5 hours until generation of gas
  2. customThe organic layer was separated
  3. washwashed with brine
  4. concentrationconcentrated
  5. dissolutionThis was dissolved in DCM (7 mL)
  6. stirringAfter being stirred at rt for 1 hour
  7. washwashed with brine
  8. dry with materialThe organic layer was dried over Na2SO4
  9. concentrationconcentrated
  10. custompurified by silica gel column chromatography (eluent: 10% MeOH in DCM)

Sources & evidence

ORD record
ord-59f1205e831b4d7bb6d744b5348f5e44
Source dataset
uspto-grants-2014_02
Patent number
US08642635B2

Reaction notes

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