Benzyl Bromide → HCID 91357348, compound

HRID 1266583Notes

Reaction equation

HRID 1266583 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C@H:4]([NH:8][S:9]([C:12]1[CH:23]=[CH:22][C:15]2[N:16]=[C:17]([S:19][CH2:20][CH3:21])[S:18][C:14]=2[CH:13]=1)(=[O:11])=[O:10])[CH:5]([CH3:7])[CH3:6].C([O-])([O-])=O.[K+].[K+].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(OC(=O)C)C>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:24])[C@H:4]([N:8]([S:9]([C:12]1[CH:23]=[CH:22][C:15]2[N:16]=[C:17]([S:19][CH2:20][CH3:21])[S:18][C:14]=2[CH:13]=1)(=[O:11])=[O:10])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH:5]([CH3:7])[CH3:6]

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 91535710HCID 91535710, compound

Product 1

HCID 91357348HCID 91357348, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(2R)-3-methyl-2-[(2-ethylthiobenzthiazol-6-sulfonyl)amino]butanoic acid methylester (0.16 g, 0.376 mmol) prepared in a similar manner as in Example 14 was dissolved in DMF (1 mL). K2CO3 (150 mg, 3 equi.) and benzylbromide (0.056 mL, 1.3 equi.) were added at RT. After stirring the reaction solution for 1 hour at RT, ethylacetate (5 mL) and H2O were added to afford the phase separation, when starting material was exhausted. The separated organic phase was washed with H2O for several times, dried over MgSO4 and distilled under reduced pressure to prepare the titled compound, (2R)-3-methyl-2-[(ethylthio-6-benzthiazolsulfonyl)benzylamino]butanoic acid methylester (180 mg, 100%).

Workup

  1. customto afford
  2. customthe phase separation, when
  3. washThe separated organic phase was washed with H2O for several times
  4. dry with materialdried over MgSO4
  5. distillationdistilled under reduced pressure
  6. customto prepare the titled compound, (2R)-3-methyl-2-[(ethylthio-6-benzthiazolsulfonyl)benzylamino]butanoic acid methylester (180 mg, 100%)

Sources & evidence

ORD record
ord-7301828c72f54dd1953d161dce23581c
Source dataset
uspto-grants-2003_04
Patent number
US06548667B2

Reaction notes

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