Trifluoroacetic anhydride → HCID 9900550, compound

HRID 1369167Notes

Reaction equation

HRID 1369167 reaction equation
[CH2:1]([O:3][C:4]1[CH:21]=[CH:20][C:7]([CH2:8][C@@H:9]([C:17]([OH:19])=O)[NH:10][C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])=[CH:6][CH:5]=1)[CH3:2].FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:7]([CH2:8][C@H:9]([NH:10][C:11](=[O:16])[C:12]([F:13])([F:14])[F:15])[C:17]2=[O:19])=[CH:20][CH:21]=1)[CH3:2]

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 12040691HCID 12040691, compound

Product 1

HCID 9900550HCID 9900550, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

O-Ethyl-N-trifluoroacetyl-L-tyrosine (XIII, Example 17, 1.52 g, 5 mmol) and ferric chloride (0.89 g, 5 mmol) are suspended in methylene chloride (36 mL). Trifluoroacetic anhydride (2.12 mL, 15 mmol) is added over 1 hr at 20-25°. The reaction is stirred for 1 hr and then quenched with water (36 mL). The organic layer is separated and mixed with methanol (7 mL). The mixture is cooled to −20° for 1 hr and then filtered to give the same title compound as EXAMPLE 4.

Workup

  1. customquenched with water (36 mL)
  2. customThe organic layer is separated
  3. additionmixed with methanol (7 mL)
  4. temperatureThe mixture is cooled to −20° for 1 hr
  5. filtrationfiltered

Sources & evidence

ORD record
ord-541e3126c31e42babc1cb2297d8ca0a8
Source dataset
uspto-grants-2003_06
Patent number
US06576769B2

Reaction notes

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