Trifluoroacetic acid → HCID 86729322, compound

HRID 1474621Notes

Reaction equation

HRID 1474621 reaction equation
[CH2:1]([O:4][C:5]1[CH:33]=[CH:32][C:8]([CH2:9][C:10]2[CH:11]=[C:12]([C@@:17]3(OC)[C@H:22]([OH:23])[C@@H:21]([OH:24])[C@H:20]([OH:25])[C:19]([CH2:28][OH:29])([CH2:26][OH:27])[O:18]3)[CH:13]=[CH:14][C:15]=2[Cl:16])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].FC(F)(F)C(O)=O>C(Cl)Cl.C(OCC)(=O)C>[CH2:1]([O:4][C:5]1[CH:33]=[CH:32][C:8]([CH2:9][C:10]2[CH:11]=[C:12]([C@@:17]34[O:18][C@@:19]([CH2:28][OH:29])([CH2:26][O:27]3)[C@@H:20]([OH:25])[C@H:21]([OH:24])[C@H:22]4[OH:23])[CH:13]=[CH:14][C:15]=2[Cl:16])=[CH:7][CH:6]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86729323HCID 86729323, compound

Product 1

HCID 86729322HCID 86729322, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S,3R,4S,55)-2-(3-(4-(allyloxy)benzyl)-4-chlorophenyl)-6,6-bis(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol (0.5 g, 1.04 mmol) in dry DCM (20 mL), was added trifluoracetic acid (4.6 mL, 62.43 mmol) dropwise at 0° C. and the reaction mixture was stirred at r.t. for 1 h. After the completion of the reaction as monitored by TLC, the reaction mixture was diluted with ethyl acetate (100 mL) and washed sequentially with water (2×10 mL) and NaHCO3 (2×10 mL). The combined organic layers were dried over anhydrous Na2SO4 and volatiles were evaporated in vacuo. The crude compound was used as such in the next reaction (440 mg, 94.3%).

Workup

  1. customAfter the completion of the reaction
  2. washwashed sequentially with water (2×10 mL) and NaHCO3 (2×10 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4 and volatiles
  4. customwere evaporated in vacuo
  5. customsuch in the next reaction (440 mg, 94.3%)

Sources & evidence

ORD record
ord-0600405f2c984c1e8a384578eceb3ef6
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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