Methanol → HCID 11718898, compound

HRID 2380851Notes

Reaction equation

HRID 2380851 reaction equation
S(Cl)([Cl:3])=O.[NH2:5][C@@:6]1([C:26]([OH:28])=[O:27])[C@H:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)[CH2:10][C@@H:9]2[C@H:7]1[C@@:8]2([F:25])[C:22]([OH:24])=[O:23].[CH3:29]O>>[ClH:3].[CH3:29][O:23][C:22]([C@:8]1([F:25])[C@@H:7]2[C@H:9]1[CH2:10][C@@H:11]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=1)[C@@:6]2([NH2:5])[C:26]([OH:28])=[O:27])=[O:24]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 9886034MGS-0039

Product 1

HCID 11718898HCID 11718898, compound

Conditions

Temperature
50 °C

Procedure

0.65 mL of thionyl chloride was added to 800 mg of (1R,2R,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid suspended in 8 mL of methanol at ice-cooling, and the mixture was stirred for 4 hours at 50° C. The mixture was further stirred for 3 hours at room temperature, and methanol was distilled under reduced pressure. After 20 mL of hexane was added to the residue, the mixture was stirred for 2 hours, and then the solids were filtered. The solids were washed with diisopropyl ether and hexane, thereby yielding 820 mg of (1R,2R,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzyloxy)-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid 6-methyl ester hydrochloride.

Workup

  1. temperaturecooling
  2. stirringThe mixture was further stirred for 3 hours at room temperature
  3. distillationmethanol was distilled under reduced pressure
  4. additionAfter 20 mL of hexane was added to the residue
  5. stirringthe mixture was stirred for 2 hours
  6. filtrationthe solids were filtered
  7. washThe solids were washed with diisopropyl ether and hexane

Sources & evidence

ORD record
ord-a98fce87d6e04e26bea93db790b72f8a
Source dataset
uspto-grants-2012_09
Patent number
US08258133B2

Reaction notes

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