Acetic Anhydride → HCID 131720814, compound

HRID 2393065Notes

Reaction equation

HRID 2393065 reaction equation
[CH3:1][C:2]([C@H:4]1[C@@H:8]2[C@@H:9]3[C@@:22]([CH3:25])([CH2:23][CH2:24][C@@:7]2([CH2:31][OH:32])[CH2:6][CH2:5]1)[C@@:21]1([CH3:26])[C@@H:12]([C@:13]2([CH3:30])[C@@H:18]([CH2:19][CH2:20]1)[C:17]([CH3:28])([CH3:27])[C@@H:16]([OH:29])[CH2:15][CH2:14]2)[CH2:11][CH2:10]3)=[CH2:3].[C:33]([O:36]C(=O)C)(=[O:35])[CH3:34]>N1C=CC=CC=1>[CH3:3][C:2]([C@H:4]1[C@@H:8]2[C@@H:9]3[C@@:22]([CH3:25])([CH2:23][CH2:24][C@@:7]2([CH2:31][OH:32])[CH2:6][CH2:5]1)[C@@:21]1([CH3:26])[C@@H:12]([C@:13]2([CH3:30])[C@@H:18]([CH2:19][CH2:20]1)[C:17]([CH3:28])([CH3:27])[C@@H:16]([OH:29])[CH2:15][CH2:14]2)[CH2:11][CH2:10]3)=[CH2:1].[C:33]([O-:36])(=[O:35])[CH3:34]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 72326Betulin

Product 1

HCID 131720814HCID 131720814, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Then, the secondary hydroxyl group of monoprotected betulin compound 4 was acetylated using acetic anhydride in pyridine (Ac2O/pyridine), to yield monoprotected betulin acetate compound 5 of scheme 2 in 87% yield. Other acetylating agents also can be used. Examples of other acetylating agents include, but are not limited to, acetyl chloride; pentafluorophenyl acetate, triethylamine, and dimethylformamide; acetic anhydride, boron trifluoride etherate, and tetrahydrofuran; ketene, potassium tert-butoxide, and tetrahydrofuran; and acetic acid and trimethylsilyl chloride.

Sources & evidence

ORD record
ord-aa279f192eda431db178ac2c07d6b0a9
Source dataset
uspto-grants-1998_09
Patent number
US05804575

Reaction notes

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