Trifluoroacetic acid → HCID 22916669, compound

HRID 1376592Notes

Reaction equation

HRID 1376592 reaction equation
C([O:5][C:6]([NH:8][CH2:9][C:10]([NH:12][CH2:13][C:14]1[S:15][CH:16]=[CH:17][N:18]=1)=[O:11])=O)(C)(C)C.[F:19][C:20]([F:25])([F:24])C(O)=O>>[F:19][C:20]([F:25])([F:24])[C:6]([NH:8][CH2:9][C:10]([NH:12][CH2:13][C:14]1[S:15][CH:16]=[CH:17][N:18]=1)=[O:11])=[O:5]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22916736HCID 22916736, compound

Product 1

HCID 22916669HCID 22916669, compoundYield 98%

Procedure

To 2.05 g of the above-obtained 2-[(N-tert-butoxycarbonylglycyl)amino]methylthiazole was added 10 ml of trifluoroacetic acid, and the mixture was stirred at room temperature for 30 minutes. The reaction solution was concentrated under reduced pressure. To the residue were added 10.74 g of ethyl trifluoroacetate and 3.83 g of triethylamine, and the mixture was stirred at room temperature for 30 minutes. The mixture was then concentrated under reduced pressure; and purified by flash column chromatography using silica gel, eluting first with ethyl acetate and then with a 20:1 mixture of ethyl acetate and methanol to give 1.98 g (yield 98%) of 2-[(N-trifluoroacetylglycyl)amino]methylthiazole as colorless crystals.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionTo the residue were added 10.74 g of ethyl trifluoroacetate and 3.83 g of triethylamine
  3. stirringthe mixture was stirred at room temperature for 30 minutes
  4. concentrationThe mixture was then concentrated under reduced pressure
  5. customand purified by flash column chromatography
  6. washeluting first with ethyl acetate
  7. additionwith a 20:1 mixture of ethyl acetate and methanol

Sources & evidence

ORD record
ord-16c35eb6468043b7a142652f8069c90b
Source dataset
uspto-grants-1997_09
Patent number
US05663162

Reaction notes

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