Diisopropylethylamine → HCID 11998435, compound

HRID 1948405Notes

Reaction equation

HRID 1948405 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[S:15][C:14]([S:16](Cl)(=[O:18])=[O:17])=[CH:13][CH:12]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2].[CH3:20][O:21][C:22](=[O:27])[CH:23]([NH2:26])[CH2:24][OH:25].CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[S:15][C:14]([S:16]([NH:26][C@H:23]([C:22]([O:21][CH3:20])=[O:27])[CH2:24][OH:25])(=[O:18])=[O:17])=[CH:13][CH:12]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 416960Methyl DL-serinateHCID 866225625-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride

Product 1

HCID 11998435HCID 11998435, compound

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

5-[2-(acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-sulfonyl chloride, prepared as in Step II of Example 1 (110 mg; 0.33 mmol; 1 eq), is dissolved in a mixture of DCM/DMF (1/1, 10 ml). 2-Amino-3-hydroxy-propionic acid methyl ester (0.2 ml; 1.65 mmol; 5 eq) and DIEA (0.17 ml; 0.98 mmol; 3 eq) are added. After one hour, the solvents are evaporated to dryness. The crude product is re-dissolved in DCM and washed with NH4Cl saturated solution, water and dried over MgSO4. After evaporation of the solvents, crude material is precipitated in ACN, affording after filtration, Compound (15) as a white powder (54 mg; 39%).

Workup

  1. customthe solvents are evaporated to dryness
  2. dissolutionThe crude product is re-dissolved in DCM
  3. washwashed with NH4Cl saturated solution, water
  4. dry with materialdried over MgSO4
  5. customAfter evaporation of the solvents, crude material
  6. customis precipitated in ACN
  7. customaffording
  8. filtrationafter filtration, Compound (15) as a white powder (54 mg; 39%)

Sources & evidence

ORD record
ord-d44866c812c4423c99cb1fa6fe138735
Source dataset
uspto-grants-2013_03
Patent number
US08399497B2

Reaction notes

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