Trifluoroacetic acid → HCID 86685124, compound

HRID 1913008Notes

Reaction equation

HRID 1913008 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:14]([O:15][CH2:16]C2C=CC=CC=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@:12]([C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([CH2:40][C:41]3[CH:46]=[CH:45][C:44]([O:47][CH2:48][CH3:49])=[C:43]([F:50])[C:42]=3[F:51])[CH:34]=2)([O:31][CH3:32])[O:11][C:10]1([CH2:54][OH:55])CO)C1C=CC=CC=1.F[C:57](F)(F)[C:58](O)=O>ClCCl>[CH2:1]([O:8][C@H:9]1[C@H:14]([O:15][CH2:16][C:58]2[CH:57]=[CH:54][CH:10]=[CH:9][CH:14]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C@:12]2([C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([CH2:40][C:41]4[CH:46]=[CH:45][C:44]([O:47][CH2:48][CH3:49])=[C:43]([F:50])[C:42]=4[F:51])[CH:34]=3)[O:11][C@@:10]1([CH2:54][OH:55])[CH2:32][O:31]2)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68015104HCID 68015104, compound

Product 1

HCID 86685124HCID 86685124, compoundYield 104.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[(3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[(4-ethoxy-2,3-difluoro-phenyl)methyl]phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-2-yl]methanol 3m (1.0 g, 1.29 mmol) was dissolved in 10 mL dichloromethane, followed by addition of trifluoroacetic acid (0.19 mL, 2.58 mmol). The reaction mixture was stirred for 4 hours. Thereafter, the reaction mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel chromatography with elution system B to obtain the title compound [(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[(4-ethoxy-2,3-difluoro-phenyl)methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]methanol 3n (500 mg, yellow grease), yield: 52.1%. MS m/z (ESI): 760.3 [M+18]. 1H NMR (400 MHz, CD3OD): δ 7.37-7.30 (m, 13H), 7.23-7.18 (m, 3H), 6.91-6.89 (m, 2H), 6.68 (dd, 1H), 6.55 (dd, 1H), 4.93-4.90 (m, 2H), 4.79-4.56 (m, 4H), 4.30-4.28 (m, 2H), 4.18-4.05 (m, 4H), 3.83-3.49 (m, 5H), 1.33 (t, 3H).

Workup

  1. concentrationThereafter, the reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was purified by silica gel chromatography with elution system B

Sources & evidence

ORD record
ord-638a0d95ec0a4596b3b228453a0dfb22
Source dataset
uspto-grants-2013_12
Patent number
US08609622B2

Reaction notes

Loading…