Potassium Carbonate → ((2'S,3'R,4'S,5'R,6'R)-3',4',5'-tris(benzyloxy)-6'-(benzyloxymethyl)-7-chloro-6-(4-ethylbenzyl)-2-methyl-3',4',5',6'-tetrahydrospiro[chroman-4,2'-pyran]-2-yl)methanol

HRID 1713609Notes

Reaction equation

HRID 1713609 reaction equation
[Cl:1][C:2]1[C:3]([CH2:53][C:54]2[CH:59]=[CH:58][C:57]([CH2:60][CH3:61])=[CH:56][CH:55]=2)=[CH:4][C:5]([C@:9]2([CH2:48][C:49]3([CH3:52])[CH2:51][O:50]3)[C@H:14]([O:15][CH2:16]C3C=CC=CC=3)[C@@H:13]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C@H:12]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C@@H:11]([CH2:39][O:40][CH2:41]C3C=CC=CC=3)[O:10]2)=[C:6]([OH:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:16]([O:15][C@@H:14]1[C@@H:13]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C@H:12]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C@@H:11]([CH2:39][O:40][CH2:41][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[O:10][C@:9]21[C:5]1[C:6](=[CH:7][C:2]([Cl:1])=[C:3]([CH2:53][C:54]3[CH:55]=[CH:56][C:57]([CH2:60][CH3:61])=[CH:58][CH:59]=3)[CH:4]=1)[O:8][C:49]([CH2:51][OH:50])([CH3:52])[CH2:48]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 866218495-chloro-4-(4-ethylbenzyl)-2-((2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-((2-methyloxiran-2-yl)methyl)tetrahydro-2H-pyran-2-yl)phenol

Product 1

HCID 68794050((2'S,3'R,4'S,5'R,6'R)-3',4',5'-tris(benzyloxy)-6'-(benzyloxymethyl)-7-chloro-6-(4-ethylbenzyl)-2-methyl-3',4',5',6'-tetrahydrospiro[chroman-4,2'-pyran]-2-yl)methanolYield 137%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 50 (19 mg, 22.6 μmol) and potassium carbonate (30 mg, 226 μmol) in DMF (2 mL) was heated to 70° C. for 2 h in a closed vial. LCMS indicated a complete conversion to a less polar product. The mixture was evaporated, and the residue was separated between water and DCM. The organic phase was dried (Na2SO4), filtered, and evaporated. The residue was purified by preparatory TLC, developed with 15% EtOAc in petroleum ether to give 51 (13 mg, 68% yield). 1H NMR (300 MHz, CDCl3) δ 7.09-7.31 (m, 19H), 6.93-7.01 (m, 4H), 6.90 (s, 1H), 6.80-6.84 (m, 2H), 4.73-4.86 (m, 3H), 4.29-4.55 (m, 3H), 4.28 (d, J=10.8 Hz, 1H), 4.09 (d, J=15.0 Hz, 1H), 4.02 (d, J=8.7 Hz, 1H), 3.69-3.93 (m, 7H), 3.17-3.38 (m, 3H), 2.49-2.59 (m, 3H), 2.20 (d, J=15.6 Hz, 1H), 1.46 (s, 3H), 1.14 (t, J=7.5 Hz, 3H).

Workup

  1. customThe mixture was evaporated
  2. customthe residue was separated between water and DCM
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by preparatory TLC

Sources & evidence

ORD record
ord-519ec74b32874b3da4cda8afce0c7ed0
Source dataset
uspto-grants-2010_09
Patent number
US07795228B2

Reaction notes

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