Water → HCID 68792675, compound

HRID 1713586Notes

Reaction equation

HRID 1713586 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@:6]1([CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][C:36]2[CH:41]=[CH:40][C:39]([CH2:42][CH3:43])=[CH:38][CH:37]=2)=[C:31]([Cl:44])[CH:30]=1)OC)(=O)[CH3:2].C1(C)C=CC=CC=1.B(F)(F)F.O(CC)CC.[OH2:61]>C(Cl)Cl>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@:6]21[C:34]1[C:29](=[CH:30][C:31]([Cl:44])=[C:32]([CH2:35][C:36]3[CH:41]=[CH:40][C:39]([CH2:42][CH3:43])=[CH:38][CH:37]=3)[CH:33]=1)[O:28][CH2:27][CH2:26]2)(=[O:61])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 8000Boron trifluoride etherateHCID 68792288HCID 68792288, compound

Product 1

HCID 68792675HCID 68792675, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(2S,3R,4S,5R,6R)-6-(Acetoxymethyl)-2-(2-(3-chloro-4-(4-ethylbenzyl)phenoxy)ethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate (18) (19 mg, 0.03 mmol) was azeotropically dried (3×) with toluene, then dissolved in CH2Cl2 (0.4 mL), cooled to 0° C., and treated with BF3—OEt2 (approx 8 drops of a 48% solution). After 24 h, the reaction was concentrated onto celite and chromatographed over SiO2 (ISCO system, 0-40% EtOAc/hexanes) to provide a film (9.6 mg, 53%). 1H NMR (300 MHz, CDCl3) δ ppm: 7.35 (s, 1H), 7.09 (s, 4H), 6.83 (s, 1H), 5.63 (d, J=9.9 Hz, 1H), 5.40 (t, J=9.6 Hz, 1H), 5.18 (t, J=10.2 Hz, 1H), 4.26-4.33 (m, 1H), 4.05-4.20 (m, 4H), 3.95 (s, 2H), 3.93 (m, 2H), 2.60 (q, J=15, 7.5 Hz, 2H), 2.04 (s, 3H), 2.04 (s, 3H), 2.01 (s, 3H), 1.83 (s, 3H), 1.21 (t, J=7.8 Hz, 3H). LC/MS 99.7% (ELSD) tR=2.93 min, calcd for C31H35ClO10: 602.19, found 620.4 (M+H2O)+.

Workup

  1. concentrationthe reaction was concentrated onto celite
  2. customchromatographed over SiO2 (ISCO system, 0-40% EtOAc/hexanes)
  3. customto provide a film (9.6 mg, 53%)

Sources & evidence

ORD record
ord-556d79632f0d4ba587c4b541ebe387cc
Source dataset
uspto-grants-2010_09
Patent number
US07795228B2

Reaction notes

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