Diethyl Ether → HCID 70083822, compound

HRID 1755825Notes

Reaction equation

HRID 1755825 reaction equation
[CH3:1][O:2][C:3](=[O:57])[C@H:4]([CH:54]([CH3:56])[CH3:55])[NH:5][C:6](=[O:53])[C@@H:7]([CH:50]([CH3:52])[CH3:51])[NH:8][C:9](=[O:49])[CH:10]([CH:12]1[CH2:18][CH2:17][N:16]([C@@H:19]([NH:21][C:22](=[O:33])[C@H:23]([CH3:32])[NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH3:20])[CH2:15][CH:14]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:13]1[O:41][Si](C(C)(C)C)(C)C)[CH3:11].[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].CCOCC>C1COCC1>[CH3:1][O:2][C:3](=[O:57])[C@H:4]([CH:54]([CH3:56])[CH3:55])[NH:5][C:6](=[O:53])[C@@H:7]([CH:50]([CH3:52])[CH3:51])[NH:8][C:9](=[O:49])[CH:10]([CH:12]1[CH2:18][CH2:17][N:16]([C@@H:19]([NH:21][C:22](=[O:33])[C@H:23]([CH3:32])[NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH3:20])[CH2:15][CH:14]([CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:13]1[OH:41])[CH3:11]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 2724141Tetrabutylammonium FluorideHCID 70084770HCID 70084770, compound

Product 1

HCID 70083822HCID 70083822, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

One isomer of the protected alcohol (66) is dissolved in THF and treated with n-Bu4NF (1M in THF, 2 equivalents) at room temperature. After all of the ether disappears (tlc), the reaction mixture is evaporated at reduced pressure and the residue is purified by flash chromatography to give the title compound (67).

Workup

  1. customthe reaction mixture is evaporated at reduced pressure
  2. customthe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-bc92e7ec30b9494fa6d707bc3e4513a1
Source dataset
uspto-grants-1995_08
Patent number
US05438118

Reaction notes

Loading…