Trifluoroacetic acid → HCID 86762168, compound

HRID 1907433Notes

Reaction equation

HRID 1907433 reaction equation
[CH:1]1([NH:6][C:7]2[CH:8]=[CH:9][C:10]([F:30])=[C:11]([C@@:13]34[O:21][CH2:20][CH2:19][C@@H:18]3[CH2:17][S:16][C:15]([NH:22]C(=O)OC(C)(C)C)=[N:14]4)[CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:1]1([NH:6][C:7]2[CH:8]=[CH:9][C:10]([F:30])=[C:11]([C@@:13]34[O:21][CH2:20][CH2:19][C@@H:18]3[CH2:17][S:16][C:15]([NH2:22])=[N:14]4)[CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86762159HCID 86762159, compound

Product 1

HCID 86762168HCID 86762168, compoundYield 137%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (±)-((4aS,7aS)-7a-(5-(cyclopentylamino)-2-fluorophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-yl)carbamate (16 mg, 0.037 mmol) and TFA (56.6 μL, 0.735 mmol) in DCM (245 μL) was stirred at rt for 3 h. The solvents were removed to give (4aS,7aS)-7a-(5-(cyclopentylamino)-2-fluorophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-amine (17 mg) as its TFA salt as a colorless oil. MS (M+H)+: 336.02.

Workup

  1. customThe solvents were removed

Sources & evidence

ORD record
ord-819771ca152f4214ab4144538286eeb3
Source dataset
uspto-grants-2013_12
Patent number
US08598161B2

Reaction notes

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