1,1-Dichloroethane → HCID 57979763, compound

HRID 1868026Notes

Reaction equation

HRID 1868026 reaction equation
[CH3:1][S:2]([O:5][C@H:6]([CH3:30])[CH2:7][N:8]([C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])[CH2:9][C@@H:10]([NH:12]C(OC(C)(C)C)=O)[CH3:11])(=[O:4])=[O:3].C(O)(C(F)(F)F)=O.ClC(Cl)C>ClCCl>[CH3:1][S:2]([O:5][C@H:6]([CH3:30])[CH2:7][N:8]([CH2:9][C@@H:10]([NH2:12])[CH3:11])[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 63651,1-DichloroethaneHCID 6422Trifluoroacetic acid2×HCID 57979758HCID 57979758, compound

Product 1

HCID 57979763HCID 57979763, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of (1R)-2-([(benzyloxy)carbonyl]{(2S)-2-[(tert-butoxycarbonyl)amino]propyl}amino)-1-methylethyl methanesulfonate (2.29 g, 5.15 mmol) in anhydrous dichloromethane (38 mL) was added TFA (38 mL) dropwise at 0° C. The reaction mixture was stirred at room temperature for 1 hour. Reaction was complete as determined by TLC. Most of TFA was azeotropped with dichloroethane. The residue was then diluted with dichloromethane and washed with 2N Na2CO3 (aq.), organic layer was dried over MgSO4. Solvent evaporation afforded (R)-1-(((S)-2-aminopropyl)(benzyloxycarbonyl)amino)propan-2-yl methanesulfonate in quantitative yield (1.8 g) as oil. It was carried to the next step immediately.

Workup

  1. customReaction
  2. washwashed with 2N Na2CO3 (aq.), organic layer
  3. dry with materialwas dried over MgSO4
  4. customSolvent evaporation

Sources & evidence

ORD record
ord-9a386c9fc92f4c638336695115c61f61
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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