Hydrochloric Acid → HCID 11998547, compound

HRID 1948406Notes

Reaction equation

HRID 1948406 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[S:15][C:14]([S:16]([NH:19][C@H:20]([C:23]([O:25]C)=[O:24])[CH2:21][OH:22])(=[O:18])=[O:17])=[CH:13][CH:12]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2].[OH-].[Na+].Cl>C1COCC1>[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[S:15][C:14]([S:16]([NH:19][C@H:20]([C:23]([OH:25])=[O:24])[CH2:21][OH:22])(=[O:17])=[O:18])=[CH:13][CH:12]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11998435HCID 11998435, compound

Product 1

HCID 11998547HCID 11998547, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methyl N-({5-[2-(acetylamino)-4-methyl-1,3-thiazol-5-yl]-2-thienyl}sulfonyl)serinate (15) (48 mg; 0.11 mmol; 1 eq), is dissolved in THF (2 ml). The resulting solution is cooled down to 0° C. and sodium hydroxide (5M) (0.3 ml; 14 mmol; 12.5 eq) is added slowly. The reaction mixture is stirred at room temperature for 30 minutes, then neutralized with HCl (1M). The solvents are evaporated to dryness and the expected compound is extracted with EtOAc (3 times) and dried over MgSO4. After evaporation of the solvents, crude material is precipitated in ACN, affording after filtration, Compound (16) as a white solid (5 mg; 10%).

Workup

  1. customThe solvents are evaporated to dryness
  2. extractionthe expected compound is extracted with EtOAc (3 times)
  3. dry with materialdried over MgSO4
  4. customAfter evaporation of the solvents, crude material
  5. customis precipitated in ACN
  6. customaffording
  7. filtrationafter filtration, Compound (16) as a white solid (5 mg; 10%)

Sources & evidence

ORD record
ord-988d486892d0496aa164456a71a16132
Source dataset
uspto-grants-2013_03
Patent number
US08399497B2

Reaction notes

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