Chlorine → HCID 131719928, compound

HRID 649803Notes

Reaction equation

HRID 649803 reaction equation
ClCl.CC(C)([O-])C.[K+].[C:9]([CH:12]([CH:14]([C:16]([OH:18])=[O:17])[OH:15])[OH:13])([OH:11])=[O:10].[CH2:19]([S:23][C:24]1[C:28]([C@@H:29]2[CH2:35][N:34]3[CH2:36][C@H:30]2[CH2:31][CH2:32][CH2:33]3)=[N:27][S:26][N:25]=1)[CH2:20][CH2:21][CH3:22]>C1(C)C=CC=CC=1>[C:9]([C@@H:12]([C@H:14]([C:16]([OH:18])=[O:17])[OH:15])[OH:13])([OH:11])=[O:10].[CH2:19]([S:23][C:24]1[C:28]([C@@H:29]2[CH2:35][N:34]3[CH2:36][C@H:30]2[CH2:31][CH2:32][CH2:33]3)=[N:27][S:26][N:25]=1)[CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 24526ChlorineHCID 23665647Potassium tert-butoxideHCID 70236903HCID 70236903, compound

Product 1

HCID 131719928HCID 131719928, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Starting from a mixture of (5S,6S)- and (5S,6R)-6-(3-chloro-1,2,5-thiadiazol-4-yl)-1-azabicyclo[3.2.1]octane described in example 63C, the chlorine was substituted with butylthio as described in example 14. A 1:9 mixture of (5S,6S)- and (5S,6R)-6-(3-butylthio-1,2,5-thiadiazol-4-yl)-1-azabicyclo[3.2.1]octane (10 g, 35 mmol) was dissolved in toluene (40 ml) and treated with potassium tertbutoxide (0.5 g) at reflux for 1 hour. The toluene solution was washed with water (15 ml) dried and evaporated. The residue crystallized with (+) L-tartaric acid giving the optical pure title compound in 12.5 g yield. (Compound 111). M.p. 128-129° C.

Workup

  1. temperatureat reflux for 1 hour
  2. washThe toluene solution was washed with water (15 ml)
  3. customdried
  4. customevaporated
  5. customThe residue crystallized with (+) L-tartaric acid giving the optical pure title compound in 12.5 g
  6. customyield

Sources & evidence

ORD record
ord-0967ac801a3f47d98cbbd6326c140709
Source dataset
uspto-grants-2001_08
Patent number
US06271229B1

Reaction notes

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