Acetic Anhydride → HCID 58746504, compound

HRID 724637Notes

Reaction equation

HRID 724637 reaction equation
[NH2:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:17](=[O:19])(=[O:18])[NH:16][C:15](=[O:20])[CH:14]=2)=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].[C:21](OC(=O)C)(=[O:23])[CH3:22].C(N(CC)C(C)C)(C)C>CN1CCCC1=O.CS(C)=O>[C:21]([NH:1][C@@H:2]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[S:17](=[O:19])(=[O:18])[NH:16][C:15](=[O:20])[CH:14]=2)=[CH:11][CH:12]=1)[C:3]([OH:5])=[O:4])(=[O:23])[CH3:22]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 69597707HCID 69597707, compound

Product 1

HCID 58746504HCID 58746504, compoundYield 120.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

(2S)-2-amino-3-[4-(1,1-dioxido-3-oxo-2,3-dihydroisothiazol-5-yl)phenyl]propanoic acid (45 mg, 0.15 mmol) was dissolved in N-methylpyrrolidinone (1.0 mL) with 20 drops of DMSO added to fully dissolve. To the solution was added acetic anhydride (14 μL, 0.15 mmol) and N,N-diisopropylethylamine (79 μL, 0.46 mmol). The solution was stirred at room temperature for 2 h. The product was purified by preparative LCMS to afford the desired product (61 mg, 96%). LCMS found for C14H15N2O6S (M+H)+: m/z=339.1

Workup

  1. additionadded
  2. dissolutionto fully dissolve
  3. customThe product was purified by preparative LCMS

Sources & evidence

ORD record
ord-53c45c702ea84627bb1c78fe05b45611
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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