Ethanol → HCID 86695226, compound

HRID 1504064Notes

Reaction equation

HRID 1504064 reaction equation
[Cl:1][C:2]1[C:3]2[C:4]3[CH:5]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:6][CH2:7][CH2:8][C:9]=3[S:10][C:11]=2[N:12]=[CH:13][N:14]=1.CCO>CO>[Cl:1][C:2]1[C:3]2[C:4]3[C@@H:5]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:6][CH2:7][CH2:8][C:9]=3[S:10][C:11]=2[N:12]=[CH:13][N:14]=1.[Cl:1][C:2]1[C:3]2[C:4]3[C@H:5]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:6][CH2:7][CH2:8][C:9]=3[S:10][C:11]=2[N:12]=[CH:13][N:14]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 89691359HCID 89691359, compound

Product 2

HCID 86695226HCID 86695226, compoundYield 37%HCID 89691340HCID 89691340, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The enantiomers of racemic ethyl 2-[3-chloro-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-13-yl]acetate (1.4 g, 4.50 mmol, 1.00 equiv) in MeOH (10 mL) were separated by preparative chiral HPLC under the following conditions: column: Chiralpak IC 0.46*25 cm, 5 um; mobile phase, Hex (0.1% TEA): EtOH=70:30; UV detection at 254 nm. The product-containing fractions were collected and evaporated to remove solvents under reduced pressure to give 520 mg (37%) of ethyl 2-[(13R)-3-chloro-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-13-yl]acetate 170.1 (first peak) as a white solid and 520 mg (37%) of ethyl 2-[(13S)-3-chloro-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-13-yl]acetate 170.2 (second peak) as a white solid, respectively.

Workup

  1. customThe product-containing fractions were collected
  2. customevaporated
  3. customto remove solvents under reduced pressure

Sources & evidence

ORD record
ord-e53998dd592c42f28205627bca1b2bfc
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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