Acetate → HCID 86733022, compound

HRID 1580920Notes

Reaction equation

HRID 1580920 reaction equation
[CH3:1][C@H:2]1[CH2:30][O:29][C@@:5]2([O:9][C@H:8]3[CH2:10][C@H:11]4[C@@H:16]5[CH2:17][CH2:18][C@H:19]6[CH2:24][C@@H:23]([OH:25])[CH2:22][CH2:21][C@:20]6([CH3:26])[C@H:15]5[CH2:14][CH2:13][C@:12]4([CH3:27])[C@H:7]3[C@@H:6]2[CH3:28])[CH2:4][CH2:3]1.C[C@H]1C[O:61][C@@:35]2([O:39][C@H]3C[C@H]4[C@@H]5CC[C@@]6(C)C[C@@H](O)CC[C@]6(C)[C@H]5CC(=O)[C@]4(C)[C@H]3[C@@H]2C)[CH2:34]C1.C[C@H]1CO[C@@]2(O[C@H]3C[C@H]4[C@@H]5CC[C@H]6C[C@@H](O)CC[C@]6(C)C5=CC(=O)[C@]4(C)[C@H]3[C@@H]2C)CC1.C([O-])(=O)C>CO>[CH3:1][C@H:2]1[CH2:30][O:29][C@@:5]2([O:9][C@H:8]3[CH2:10][C@H:11]4[C@@H:16]5[CH2:17][CH2:18][C@H:19]6[CH2:24][C@@H:23]([OH:25])[CH2:22][CH2:21][C@:20]6([CH3:26])[C@H:15]5[CH2:14][CH2:13][C@:12]4([CH3:27])[C@H:7]3[C@@H:6]2[CH3:28])[CH2:4][CH2:3]1.[C:35]([O-:61])(=[O:39])[CH3:34]

Participants

6

Reactant 4

HCID 175AcetateHCID 99516TigogeninHCID 150110793514-26-9HCID 44289094HCID 44289094, compound

Product 1

HCID 86733022HCID 86733022, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.5g sapogenin obtained from Agave lentonaceum from the Republic of Honduras was found to be about 80% tigogenin by TLC. The remainder was hecogenin and 9(11)-dehydrohecogenin. This material was acetylated as described in Example I. The crude acetate was dissolved by refluxing with liberal quantities of methanol. The clear solution was evaporated to a final volume of 70ml and allowed to cool slowly to ambient temperature. The resulting crystals were filtered, washed with a little methanol, collected and dried. 1.8g of tigogenin acetate was obtained, m.p. 202°-206°, (α)D, -75°(Chlf). TLC showed this material to be better than 95% pure.

Workup

  1. customThe clear solution was evaporated to a final volume of 70ml
  2. filtrationThe resulting crystals were filtered
  3. washwashed with a little methanol
  4. customcollected
  5. customdried

Sources & evidence

ORD record
ord-404583fdecb34347a36999787192933d
Source dataset
uspto-grants-1976_01
Patent number
US03935194

Reaction notes

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