Trifluoroacetic acid → HCID 54162881, compound

HRID 1376627Notes

Reaction equation

HRID 1376627 reaction equation
C([O:5][C:6]([NH:8][C@H:9]([C:12]([NH:14][CH2:15][C:16]1[S:17][CH:18]=[CH:19][N:20]=1)=[O:13])[CH2:10][OH:11])=O)(C)(C)C.[F:21][C:22]([F:27])([F:26])C(O)=O.FC(F)(F)C(OCC)=O>C(N(CC)CC)C>[F:21][C:22]([F:27])([F:26])[C:6]([NH:8][C@H:9]([C:12]([NH:14][CH2:15][C:16]1[S:17][CH:18]=[CH:19][N:20]=1)=[O:13])[CH2:10][OH:11])=[O:5]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 9794Ethyl trifluoroacetateHCID 54488002HCID 54488002, compound

Product 1

HCID 54162881HCID 54162881, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A 1.540 g portion of 2-[(N-tert-butoxycarbonyl-L-seryl)amino]methylthiazole and 15 ml of trifluoroacetic acid were added, and the mixture was stirred for 30 minutes. The reaction mixture was concentrated to dryness under reduced pressure. To the solution of (L-seryl)aminomethylthiazole trifluoroacetatate salt thus obtained in 50 ml of methylene chloride were added with stirring 2.73 g of triethylamine and 3.84 g of ethyl trifluoroacetate. The mixture was stirred at room temperature for 3 hours, concentrated under reduced pressure and subjected to flash column chromatography on silica gel (eluted with ethyl acetate) to give 1.519 g of 2-[(N-trifluoroacetyl-L-seryl)amino]methylthiazole. Quantitative yield. NMR (CDCl3) δ: 1.5-1.75 (1H, br), 3.69 (1H, dd, J=11.5 Hz, 6.7 Hz), 4.18 (1H, dd, J=11.5 Hz, 3.5 Hz), 4.58 (1H, td, J=11.5 Hz, 3.5 Hz), 4.75 (1H, dd, J=16.7 Hz, 5.5 Hz), 4.96 (1H, dd, J=16.7 Hz, 6.9 Hz), 7.01-7.07 (1H, br), 7.31 (1H, d, J=3.3 Hz), 7.60-7.70 (1H, br), 7.68 (1H, d, J=3.3 Hz).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  2. customthus obtained in 50 ml of methylene chloride
  3. additionwere added
  4. stirringThe mixture was stirred at room temperature for 3 hours
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5b75bd8979e044e08744b66bc456fd18
Source dataset
uspto-grants-1997_09
Patent number
US05663162

Reaction notes

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