Trifluoroacetic acid → HCID 57504903, compound

HRID 2060773Notes

Reaction equation

HRID 2060773 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]23[CH2:16][CH2:15][CH2:14][CH:13]2[CH2:12][S:11][C:10]([NH:17]C(=O)OC(C)(C)C)=[N:9]3)=[CH:4][C:3]=1[O:25][CH3:26].C(O)(C(F)(F)F)=O>C(Cl)Cl.O.[OH-].[Na+]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]23[CH2:16][CH2:15][CH2:14][CH:13]2[CH2:12][S:11][C:10]([NH2:17])=[N:9]3)=[CH:4][C:3]=1[O:25][CH3:26]

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57504904HCID 57504904, compound

Product 1

HCID 57504903HCID 57504903, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution tert-butyl 7a-(4-fluoro-3-methoxyphenyl)-4,4a,5,6,7,7a-hexahydrocyclopenta[d][1,3]thiazin-2-ylcarbamate (1.04 g, 2.73 mmol) in CH2Cl2 (20 mL) is added TFA (5 mL) and the reaction is stirred at room temperature for 16 hr. The solvent is removed under reduced pressure to give a residue that is diluted with water and 5N NaOH. The aqueous layer is extracted four times with EtOAc. The organic layer is dried over Na2SO4 and the solvent is removed under reduced pressure. The crude product is purified with a 10 g SCX column using 4:1 CH2Cl2:MeOH and then 2:1 CH2Cl2: 7 N NH3 in MeOH to elute the product and give the title compound (0.756 g, 99%). ES/MS m/e: 281 (M+1).

Workup

  1. customThe solvent is removed under reduced pressure
  2. customto give a residue that
  3. extractionThe aqueous layer is extracted four times with EtOAc
  4. dry with materialThe organic layer is dried over Na2SO4
  5. customthe solvent is removed under reduced pressure
  6. customThe crude product is purified with a 10 g SCX column
  7. washMeOH and then 2:1 CH2Cl2: 7 N NH3 in MeOH to elute the product

Sources & evidence

ORD record
ord-e7ccf576c68b491a85b7f8023dbff14b
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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