Diazomethane → HCID 131712292, compound

HRID 1277609Notes

Reaction equation

HRID 1277609 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH:14]1[O:19][CH:18]([O:20][CH:21]2[CH:26]([O:27][C:28](/[CH:30]=[CH:31]/[CH:32]=[CH:33]/[CH2:34][CH:35]([OH:47])/[C:36](/[CH3:46])=[CH:37]/[CH:38]=[CH:39]/[CH2:40][CH2:41][CH:42]([CH2:44][CH3:45])[CH3:43])=[O:29])[CH:25]([OH:48])[C:24]3([O:56][CH2:55][C:54]4[C:49]3=[C:50]([OH:58])[CH:51]=[C:52]([OH:57])[CH:53]=4)[O:23][CH:22]2[CH2:59][OH:60])[CH:17]([OH:61])[CH:16]([OH:62])[CH:15]1[OH:63])=[O:11].[N+](=C)=[N-]>O1CCOCC1.CCOCC>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH:14]1[O:19][CH:18]([O:20][CH:21]2[CH:26]([O:27][C:28](/[CH:30]=[CH:31]/[CH:32]=[CH:33]/[CH2:34][CH:35]([OH:47])/[C:36](/[CH3:46])=[CH:37]/[CH:38]=[CH:39]/[CH2:40][CH2:41][CH:42]([CH2:44][CH3:45])[CH3:43])=[O:29])[CH:25]([OH:48])[C:24]3([O:56][CH2:55][C:54]4[C:49]3=[C:50]([OH:58])[CH:51]=[C:52]([OH:57])[CH:53]=4)[O:23][CH:22]2[CH2:59][OH:60])[CH:17]([OH:61])[CH:16]([OH:62])[CH:15]1[OH:63])=[O:11].[CH3:10][O:12][CH3:13]

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 644436961036-46-22×

Product 1

HCID 131712292HCID 131712292, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

The antibiotic Papulacandin A is methylated as follows: A solution of 2 g of Papulacandin A in 100 ml of dioxan is allowed to stand at 0° C. for 30 minutes with a solution of diazomethane in ether. After having evaporated off the solvent the residue is chromatographed on a silica gel column (200 g) with chloroform and increasing amounts of methanol (5 to 20%) as eluents. Colorless, amorphous Papulacandin A-monomethyl ether is obtained after precipitation from acetone/ether/hexane. The IR-spectrum (in KBr) shows the following bands: 3500, 2970, 2950, 1710, 1645, 1625, 1465, 1445, 1350, 1270, 1155, 1065, 1035, 1010 cm-1. The UV-spectrum (in ethanol) shows the following maximum values: λmax. (εmax.): 237 (34000), 263 (41600). The 13C-NMR-spectrum shows the presence of an additional methyl group. Papulacandin A-dimethyl ether, in which the 13C-NMR-spectrum shows that two additional methyl groups are present, is obtained as further product.

Workup

  1. customAfter having evaporated off the solvent the residue
  2. customis chromatographed on a silica gel column (200 g) with chloroform
  3. temperatureincreasing amounts of methanol (5 to 20%) as eluents

Sources & evidence

ORD record
ord-1afc848e0b974e948f4fd379eb2bd52b
Source dataset
uspto-grants-1981_07
Patent number
US04278665

Reaction notes

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