915-35-5 → HCID 44289094, compound

HRID 1580919Notes

Reaction equation

HRID 1580919 reaction equation
[CH3:1][C@H:2]1[CH2:34][O:33][C@@:5]2([O:9][C@H:8]3[CH2:10][C@H:11]4[C@@H:17]5[CH2:18][CH2:19][C@H:20]6[CH2:25][C@@H:24]([O:26]C(C)=O)[CH2:23][CH2:22][C@:21]6([CH3:30])[C@H:16]5[CH2:15][C:13](=[O:14])[C@:12]4([CH3:31])[C@H:7]3[C@@H:6]2[CH3:32])[CH2:4][CH2:3]1.[CH3:35][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)[C@H]5CC[C@]4(C)[C@H]3[C@@H]2C)CC1.C([O-])(=O)C>>[CH3:1][C@H:2]1[CH2:34][O:33][C@@:5]2([O:9][C@H:8]3[CH2:10][C@H:11]4[C@@H:17]5[CH2:18][CH2:19][C@@:20]6([CH3:35])[CH2:25][C@@H:24]([OH:26])[CH2:23][CH2:22][C@:21]6([CH3:30])[C@H:16]5[CH2:15][C:13](=[O:14])[C@:12]4([CH3:31])[C@H:7]3[C@@H:6]2[CH3:32])[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 101906915-35-5HCID 86733022HCID 86733022, compound

Product 1

HCID 44289094HCID 44289094, compound

Procedure

This material was recrystallized by dissolving in 300ml of heptane at reflux temperature. The clear solution was concentrated to 65ml, cooled to ambient temperature, and the crystallization product filtered. Washing with a little heptane, collection and drying gave 1.9g of material in well developed prismatic crystals of slightly green color (chlorophyll), and which on TLC (80% benzene, 20% ethyl acetate) analyzed as essentially hecogenin acetate with only a shade of the tigogenin acetate (corresponding to 0.95H and 0.05% approximately). M.p: 243°-244°C., Saponification gave hecogenin m.p. 262°-263°.

Sources & evidence

ORD record
ord-26f09e7ee7fb43bb9c583308799b7529
Source dataset
uspto-grants-1976_01
Patent number
US03935194

Reaction notes

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