Acetic Anhydride → HCID 54363709, compound

HRID 1376623Notes

Reaction equation

HRID 1376623 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 54162880HCID 54162880, compound

Product 1

HCID 54363709HCID 54363709, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1.965 g of the above-obtained 2-[(N-trifluoroacetyl-D-seryl)amino]methylthiazole in 20 ml of pyridine was added 2 ml of acetic anhydride. The mixture was stirred at room temperature for 14 hours, and then concentrated to dryness under reduced pressure. The residue was dissolved in 50 ml of methylene chloride, and the solution was washed with 30 ml of a saturated aqueous solution of sodium hydrogencarbonate. The aqueous layer was extracted with 30 ml of methylene chloride. The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated to dryness under reduced pressure to give 2.07 g (yield 92%) of 2-[(O-acetyl-N-trifluoroacetyl-D-seryl)amino]methylthiazole. NMR (CDCl3) d: 2.05 (3H, s), 4.36-4.41 (1H, m), 4.77-4.85 (2H, m), 7.33 (1H, d, J=3.3 Hz), 7.42-7.52 (1H, br), 7.6-7.7 (1H, br), 7.72 (1H, d, J=3.3 Hz) MS (EI, CHCl3, 160° C.): 339 (M+)

Workup

  1. concentrationconcentrated to dryness under reduced pressure
  2. dissolutionThe residue was dissolved in 50 ml of methylene chloride
  3. washthe solution was washed with 30 ml of a saturated aqueous solution of sodium hydrogencarbonate
  4. extractionThe aqueous layer was extracted with 30 ml of methylene chloride
  5. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  6. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-17db54e472f14e02a7f8a62db8d02eab
Source dataset
uspto-grants-1997_09
Patent number
US05663162

Reaction notes

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