Acetic Anhydride → HCID 54363710, compound

HRID 1376628Notes

Reaction equation

HRID 1376628 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]([NH:5][C@H:6]([C:9]([NH:11][CH2:12][C:13]1[S:14][CH:15]=[CH:16][N:17]=1)=[O:10])[CH2:7][OH:8])=[O:4].[C:20](OC(=O)C)(=[O:22])[CH3:21]>N1C=CC=CC=1>[C:20]([O:8][CH2:7][C@@H:6]([C:9]([NH:11][CH2:12][C:13]1[S:14][CH:15]=[CH:16][N:17]=1)=[O:10])[NH:5][C:3](=[O:4])[C:2]([F:18])([F:1])[F:19])(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 54162881HCID 54162881, compound

Product 1

HCID 54363710HCID 54363710, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To the solution of 1.518 g of 2-[(N-trifluoroacetyl-L-seryl)amino]methylthiazole in 18 ml of pyridine was added 1.8 ml of acetic anhydride, and the mixture was stirred at room temperature for 14 hours. After the reaction mixture was concentrated to dryness under reduced pressure, it was dissolved in 40 ml of methylene chloride and washed with 25 ml of a saturated aqueous sodium hydrogen carbonate solution. The aqueous layer was re-extracted with 30 ml of methylene chloride. The combined organic layer was dried with anhydrous magnesium sulfate and concentrated to dryness under reduced pressure to give 1.733 g of 2-[(O -acetyl-N-trifluoroacetyl-L-seryl)amino]methylthiazole. Quantitative yield. NMR (CDCl3) δ: 2.06 (3H, s), 4.36-4.40 (2H, m), 4.75-4.85 (3H, m), 7.17-7.26 (1H, br), 7.34 (1H, d, J=3.3 Hz), 7.73 (1H, d, J=3.3 Hz).

Workup

  1. concentrationAfter the reaction mixture was concentrated to dryness under reduced pressure, it
  2. dissolutionwas dissolved in 40 ml of methylene chloride
  3. washwashed with 25 ml of a saturated aqueous sodium hydrogen carbonate solution
  4. extractionThe aqueous layer was re-extracted with 30 ml of methylene chloride
  5. dry with materialThe combined organic layer was dried with anhydrous magnesium sulfate
  6. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-3618199073744a4892e016a6524af43d
Source dataset
uspto-grants-1997_09
Patent number
US05663162

Reaction notes

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