Methanol → HCID 15907893, compound

HRID 2182119Notes

Reaction equation

HRID 2182119 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([CH3:24])[CH:23]=1)[NH:5][C:6]([CH2:8][C:9]1[CH:20]=[CH:19][C:12]([O:13][CH:14]([CH3:18])[C:15]([OH:17])=[O:16])=[CH:11][CH:10]=1)=[O:7].[CH2:25]=C[C@@H]1[C@@H]2C[C@@H]([C@H](O)C3C=CN=C4C=CC=CC=34)N(CC2)C1.CO>C(O)C>[CH3:24][C:22]1[CH:21]=[C:4]([CH:3]=[C:2]([CH3:1])[CH:23]=1)[NH:5][C:6]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH:14]([CH2:18][CH3:25])[C:15]([OH:17])=[O:16])=[CH:19][CH:20]=1)=[O:7]

Participants

5

Reactant 3

HCID 887Methanol2×HCID 101744CinchonidineHCID 15907892HCID 15907892, compound

Product 1

HCID 15907893HCID 15907893, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Following the same procedure as described for (−) (18), cinchonidine (8.61 g, 29.3 mmol) in hot ethanol (175 mL) was added to a solution of (±)20 (10.0 g, 29.3 mmol) in hot ethanol. The solution was allowed to cool to room temperature and a portion of the solvent was removed under reduced pressure. Crystals obtained were collected by filtration, 6.6 g, mp 204-205° C. The optical rotation was measured at 21° C.: [α]D−73.3° (c=0.5, methanol). The salt was recrystallized from ethanol to give fluffy white crystals, 3.7 g, mp 206-207° C. The optical rotation was measured at 21° C.: [α]D−74.2° (c=0.5, methanol). The acid was recovered from salt, as described previously for (−)18, to obtain a white solid, 1.7 g. mp 150-15 1° C. The optical rotation was measured at 21° C.: [α]D−28.4° (c=1.2, methanol). Anal:(C20H23NO4); Calculated C 70.36, H 6.79, N 4.10; found C 70.17, H 6.86 and N 4.05

Workup

  1. customa portion of the solvent was removed under reduced pressure
  2. customCrystals obtained
  3. filtrationwere collected by filtration, 6.6 g, mp 204-205° C
  4. customwas measured at 21° C.
  5. customThe salt was recrystallized from ethanol
  6. customto give fluffy white crystals, 3.7 g, mp 206-207° C
  7. customwas measured at 21° C.
  8. customThe acid was recovered from salt
  9. customto obtain a white solid, 1.7 g
  10. custom150-15 1° C
  11. customwas measured at 21° C.

Sources & evidence

ORD record
ord-ca78c068829b49d8af1aa5b0e8c25399
Source dataset
uspto-grants-2005_05
Patent number
US06894185B2

Reaction notes

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