Trifluoroacetic acid → HCID 69082386, compound

HRID 1396252Notes

Reaction equation

HRID 1396252 reaction equation
F[C@H:2]([C@H:4]1[O:12][C@H:11]2[C@H:7]([N:8]=[C:9]([N:13]([CH3:15])[CH3:14])[S:10]2)[C@@H:6]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[C@@H:5]1[O:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=1)[CH3:3].C(O)(C(F)(F)F)=[O:37]>ClCCl>[CH3:14][N:13]([CH3:15])[C:9]1[S:10][C@H:11]2[O:12][C@H:4]([C:2](=[O:37])[CH3:3])[C@@H:5]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)[C@H:6]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[C@H:7]2[N:8]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69084882HCID 69084882, compound

Product 1

HCID 69082386HCID 69082386, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (3aR,5S,6S,7R,7aR)-5-((S)-1-fluoroethyl)-6,7-bis(4-methoxybenzyloxy)-N,N-dimethyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-amine (240 mg, 0.48 mmol) in dichloromethane (20 mL) was treated with TFA (2 mL) for 1 h at room temperature. The reaction mixture was concentrated under reduced pressure to give a residue, which was purified by Prep-HPLC under the following conditions [(Agilent 1200 prep HPLC): Column, SunFire Prep C18, 19*50 mm 5 um; mobile phase, water with 0.03% NH4OH and CH3CN (10% CH3CN up to 45% in 10 min); Detector, UV 220 nm] to afford compound 51 (Example 9) as a white solid (30 mg, 24%). (ES, m/z): [M+H]+ 265.0; 1H NMR (300 MHz, D2O) δ 6.23-6.25 (d, J=6.0 Hz, 1H), 4.93-4.99 (m, 0.5H), 4.77-4.84 (m, 0.5H), 4.17 (t, J=6.0 Hz, 1H), 4.00 (t, J=6.0 Hz, 1H), 3.71-3.74 (m, 1H), 3.36-3.49 (m, 1H), 2.94 (s, 1H), 1.25-1.35 (dd, J=6.6 Hz, 6.3 Hz, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto give a residue, which
  3. customwas purified by Prep-HPLC under the following conditions [(Agilent 1200 prep HPLC)

Sources & evidence

ORD record
ord-a07be680f4f744b5b96619af2ba93055
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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