Isopropylethanediol → HCID 86614064, compound

HRID 1727225Notes

Reaction equation

HRID 1727225 reaction equation
[Cl:1][C:2]1[C:11]2[N:10]([CH3:12])[O:9][C@H:8]3[NH:13][C@H:14]([C:16]([O:18][CH3:19])=[O:17])[CH2:15][C@@:7]3([OH:20])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH:21]([O:24][CH2:25]CO)([CH3:23])[CH3:22]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:11]2[N:10]([CH3:12])[O:9][C@H:8]3[NH:13][C@H:14]([C:16]([O:18][CH2:19][CH2:25][O:24][CH:21]([CH3:23])[CH3:22])=[O:17])[CH2:15][C@@:7]3([OH:20])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7996IsopropylethanediolHCID 11381005HCID 11381005, compound

Product 1

HCID 86614064HCID 86614064, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To methyl (2S,3aR,9bR)-6-chloro-9b-hydroxy-5-methyl-1,2,3,3a-,5,9b-hexahydropyrrolo[2,3-c][2,1]benzoxazine-2-carboxylate (Preparation 118, 0.20 g, 0.67 mmol) was added toluene (10 ml) titanium (IV) ethoxide (0.07 ml) and 2-isopropoxy ethanol. The reactants were stirred together and then heated under reflux for 1 h, before concentrating in vacuo. The crude residue was purified using a Sep Pak cartridge eluting with hexane and then hexane:ethyl acetate (50:50). Further purification by preparative HPLC was performed using a Magellan column 212×150 mm, flow rate 20 ml/min, eluting with a gradient of water:acetonitrile (55:45 to 90:10) over 8 min to yield the title compound (63.9 mg).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 h
  3. concentrationbefore concentrating in vacuo
  4. customThe crude residue was purified
  5. washeluting with hexane
  6. customFurther purification by preparative HPLC
  7. washeluting with a gradient of water:acetonitrile (55:45 to 90:10) over 8 min

Sources & evidence

ORD record
ord-9720459daff140309b7cdc109b8099c7
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

Loading…