Acetic Anhydride → HCID 57080985, compound

HRID 355316Notes

Reaction equation

HRID 355316 reaction equation
[CH2:1]([CH:4]1[CH:30]=[C:29]([CH3:31])[CH2:28][CH:27]([CH3:32])[CH2:26][CH:25]([O:33][CH3:34])[CH:24]2[O:35][C:20]([OH:39])([CH:21]([CH3:38])[CH2:22][CH:23]2[O:36][CH3:37])[C:19](=[O:40])[C:18](=[O:41])[N:17]2[CH:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)[C:11](=[O:42])[O:10][CH:9]([C:43]([CH3:61])=[CH:44][CH:45]2[CH2:50][CH2:49][CH:48]([O:51][Si:52]([C:55]([CH3:58])([CH3:57])[CH3:56])([CH3:54])[CH3:53])[CH:47]([O:59][CH3:60])[CH2:46]2)[CH:8]([CH3:62])[CH:7]([OH:63])[CH2:6][C:5]1=[O:64])[CH:2]=[CH2:3].[C:65](OC(=O)C)(=[O:67])[CH3:66]>N1C=CC=CC=1>[C:65]([O:63][CH:7]1[CH2:6][C:5](=[O:64])[CH:4]([CH2:1][CH:2]=[CH2:3])[CH:30]=[C:29]([CH3:31])[CH2:28][CH:27]([CH3:32])[CH2:26][CH:25]([O:33][CH3:34])[CH:24]2[O:35][C:20]([OH:39])([CH:21]([CH3:38])[CH2:22][CH:23]2[O:36][CH3:37])[C:19](=[O:40])[C:18](=[O:41])[N:17]2[CH:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)[C:11](=[O:42])[O:10][CH:9]([C:43]([CH3:61])=[CH:44][CH:45]2[CH2:50][CH2:49][CH:48]([O:51][Si:52]([C:55]([CH3:58])([CH3:57])[CH3:56])([CH3:53])[CH3:54])[CH:47]([O:59][CH3:60])[CH2:46]2)[CH:8]1[CH3:62])(=[O:67])[CH3:66]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 57172670HCID 57172670, compound

Product 1

HCID 57080985HCID 57080985, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 17-allyl-12-[2-(4-tert-butyl-dimethylsilyloxy-3-methoxycyclohexyl)-1-methylvinyl]-1,14-dihydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (39.9 mg) in pyridine (1.5 ml) was added acetic anhydride (0.5 ml), and the mixture was stirred at room temperature for 6 hours. The solvent was removed from the reaction mixture under reduced pressure to give a crude oil, which was purified on silica gel thin layer chromatography (developing solvent: diethyl ether and hexane, 1:1 v/v) to afford 14-acetoxy-17-allyl-12-[2-(4-tert-butyl-dimethylsilyloxy-3-methoxycyclohexyl)-1-methylvinyl]-1-hydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (26.5 g).

Workup

  1. customThe solvent was removed from the reaction mixture under reduced pressure
  2. customto give a crude oil, which
  3. customwas purified on silica gel thin layer chromatography (developing solvent: diethyl ether and hexane, 1:1 v/v)

Sources & evidence

ORD record
ord-c04ecde4520a4106aac803926445ab38
Source dataset
uspto-grants-1998_11
Patent number
US05830717

Reaction notes

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