Trifluoroacetic acid → HCID 71060799, compound

HRID 1907432Notes

Reaction equation

HRID 1907432 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]2[CH:10]=[N:11][CH:12]=[C:13]([C:15]#[C:16][CH3:17])[CH:14]=2)=[CH:4][C:3]=1[C@:18]12[O:26][CH2:25][CH2:24][C@H:23]1[CH2:22][S:21][C:20]([NH:27]C(=O)OC(C)(C)C)=[N:19]2.C(O)(C(F)(F)F)=O>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]2[CH:10]=[N:11][CH:12]=[C:13]([C:15]#[C:16][CH3:17])[CH:14]=2)=[CH:4][C:3]=1[C@:18]12[O:26][CH2:25][CH2:24][C@H:23]1[CH2:22][S:21][C:20]([NH2:27])=[N:19]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86762155HCID 86762155, compound

Product 1

HCID 71060799HCID 71060799, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (±)-tert-butyl (4aR,7aR)-7a-(2,4-difluoro-5-(5-(prop-1-ynyl)pyridin-3-yl)phenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-ylcarbamate (Preparation 6, 22 mg) in dichloromethane (300 μL) was added TFA (35 μL, 0.508 mmol) at rt, and the reaction mixture was stirred at rt for 2.5 h. The crude product was directly purified by prep TLC eluting with 90% CH2Cl2/9% MeOH/1% NH4OH to give the title compound (12 mg) a colorless oil. 1H NMR (400 MHz, CHLOROFORM-d) δ 8.66-8.61 (m, 2H), 7.86-7.83 (m, 1H), 7.71 (t, J=8.8 Hz, 1H), 6.98-6.91 (m, 1H), 4.15-4.03 (m, 2H), 3.15 (dd, J=13.1, 4.0 Hz, 1H), 3.00 (ddd, J=13.1, 7.5, 2.0 Hz, 1H), 2.80-2.73 (m, 1H), 2.24-2.09 (m, 5H). MS (M−1): 364.2.

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-e2a1e0a95db7416d9d4f03df63ff3788
Source dataset
uspto-grants-2013_12
Patent number
US08598161B2

Reaction notes

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