1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 53823001, compound

HRID 375497Notes

Reaction equation

HRID 375497 reaction equation
O.OC1C2N=NNC=2C=CC=1.[C:12]1([C:18]2([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:26]3[CH:22]([CH2:23][NH:24][CH2:25]3)[S:21](=[O:27])[CH2:20][CH2:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH3:34][N:35]([CH3:50])[CH2:36][CH:37]([O:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[CH2:46][C:47](O)=[O:48])[CH3:38].CN(C)CCCN=C=NCC>ClCCl>[CH3:50][N:35]([CH3:34])[CH2:36][CH:37]([O:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[CH2:46][C:47]([N:24]1[CH2:25][C@H:26]2[C:18]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:19][CH2:20][S@@:21](=[O:27])[C@H:22]2[CH2:23]1)=[O:48])[CH3:38]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 18995289(-)-4,4-Diphenylperhydrothiopyrano[2,3-c]pyrrole 1-oxideHCID 53734286[(3-Dimethylamino-2-propoxy)phenyl]acetic acidHCID 178526939HCID 178526939, compound

Product 1

HCID 53823001HCID 53823001, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

0.03 g of hydroxybenzotriazole hydrate is added to a solution, cooled to 0° C., of 1.06 g of (1R*, 4aR*, 7aR*) -(-) -4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole 1-oxide and 0.81 g of 2-[(3-dimethylamino-2-propoxy)phenyl]acetic acid in 60 cm3 of dry dichloromethane, followed by 0.77 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide. After stirring for 2 hours at 0° C. and 20 hours at 20° C., the reaction mixture is washed with 20 cm3 of water and then dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a silica gel column (particle size 0.04-0.06 mm, diameter 2.4 cm, height 35 cm), eluting under a nitrogen pressure of 0.6 bar with an ethyl acetate, acetic acid and water mixture (60/10/10 by volume) and collecting fractions of 50 cm3. Fractions 8 to 19 are pooled and concentrated to dryness under reduced pressure (2.7 kPa). The residue is taken up in 60 cm3 of dichloromethane, the solution is washed with 20 cm3 of a 1N aqueous solution of sodium hydroxide, dried over magnesium sulphate and then concentrated to dryness. The solid obtained is recrystallized from an ethyl acetate and ethyl ether mixture, the crystals are washed with diisopropyl oxide, drained and dried. 0.99 g of (1R*,4aR*,7aR*)-(-)-6-{2-[(3-dimethylamino2-propoxy)phenyl]acetyl}-4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole 1-oxide is obtained in the form of a white solid; melting point 120° C. [α]D20 =-323° ; (c=0.5; acetic acid).

Workup

  1. washthe reaction mixture is washed with 20 cm3 of water
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. customThe residue is chromatographed on a silica gel column (particle size 0.04-0.06 mm, diameter 2.4 cm, height 35 cm)
  5. washeluting under a nitrogen pressure of 0.6 bar with an ethyl acetate, acetic acid and water mixture (60/10/10 by volume)
  6. customcollecting fractions of 50 cm3
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  8. washthe solution is washed with 20 cm3 of a 1N aqueous solution of sodium hydroxide
  9. dry with materialdried over magnesium sulphate
  10. concentrationconcentrated to dryness
  11. customThe solid obtained
  12. customis recrystallized from an ethyl acetate and ethyl ether mixture
  13. washthe crystals are washed with diisopropyl oxide
  14. customdried

Sources & evidence

ORD record
ord-cff01444ac054e8795593bc9d05719e5
Source dataset
uspto-grants-1996_01
Patent number
US05484942

Reaction notes

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