Trifluoroacetic acid → HCID 86762162, compound

HRID 1907429Notes

Reaction equation

HRID 1907429 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:4][C:3]=1[C@:17]12[O:25][CH2:24][CH2:23][C@H:22]1[CH2:21][S:20][C:19]([NH:26]C(=O)OC(C)(C)C)=[N:18]2.C(O)(C(F)(F)F)=O>ClCCl>[NH2:26][C:19]1[S:20][CH2:21][C@@H:22]2[CH2:23][CH2:24][O:25][C@:17]2([C:3]2[CH:4]=[C:5]([NH:8][C:9](=[O:16])[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=3)[CH:6]=[CH:7][C:2]=2[F:1])[N:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86762163HCID 86762163, compound

Product 1

HCID 86762162HCID 86762162, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl ((4aR,7aR)-7a-(2-fluoro-5-(picolinamido)phenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-yl)carbamate (Preparation 5, 12 mg, 0.025 mmol) in dichloromethane (254 μL) was added TFA (39.1 μL, 0.508 mmol) at rt, and the reaction mixture was stirred at rt for 3 h. The crude product was directly purified by prep TLC eluting with 90% CH2Cl2/9% MeOH/1% NH4OH to give the title compound (5 mg, 0.013 mmol, 52.9% yield) a colorless oil. 1H NMR (500 MHz, CHLOROFORM-d) δ 10.04 (s, 1H), 8.68-8.62 (m, 1H), 8.31 (dt, J=7.8, 1.0 Hz, 1H), 8.01 (ddd, J=8.9, 4.1, 2.9 Hz, 1H), 7.93 (td, J=7.7, 1.7 Hz, 1H), 7.72 (dd, J=6.9, 2.8 Hz, 1H), 7.51 (ddd, J=7.5, 4.8, 1.1 Hz, 1H), 7.08 (dd, J=10.9, 8.8 Hz, 1H), 4.11 (t, J=7.2 Hz, 3H), 3.50 (s, 1H), 3.15 (dd, J=12.8, 4.0 Hz, 1H), 2.97 (ddd, J=13.0, 7.5, 1.8 Hz, 1H), 2.77 (dd, J=7.0, 4.0 Hz, 1H), 2.22-1.98 (m, 2H). MS (M−1): 371.2.

Workup

  1. customThe crude product was directly purified by prep TLC
  2. washeluting with 90% CH2Cl2/9% MeOH/1% NH4OH

Sources & evidence

ORD record
ord-61df9aa8ba1f42a489a2aec4d3edde6d
Source dataset
uspto-grants-2013_12
Patent number
US08598161B2

Reaction notes

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