Sulfuric Acid → HCID 15032032, compound

HRID 1761660Notes

Reaction equation

[CH3:1][C:2]([CH3:45])([C:37]1[CH:42]=[C:41]([CH3:43])[CH:40]=[CH:39][C:38]=1[OH:44])[CH2:3][N:4]1[C:9](=[O:10])[N:8]([CH2:11][C:12]([C:15]2[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=2[OH:22])([CH3:14])[CH3:13])[C:7](=[O:23])[N:6]([CH2:24][C:25]([C:28]2[CH:33]=[C:32]([CH3:34])[CH:31]=[CH:30][C:29]=2[OH:35])([CH3:27])[CH3:26])[C:5]1=[O:36].OS(O)(=O)=O>[N+](C1C=CC=CC=1)([O-])=O.C(OCC)(=O)C>[CH3:14][C:12]([CH3:13])([C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([C:12]([CH3:14])([CH3:13])[CH3:11])[C:16]=1[OH:22])[CH2:11][N:8]1[C:7](=[O:23])[N:6]([CH2:24][C:25]([C:28]2[CH:33]=[C:32]([CH3:34])[CH:31]=[C:30]([C:2]([CH3:1])([CH3:3])[CH3:37])[C:29]=2[OH:35])([CH3:26])[CH3:27])[C:5](=[O:36])[N:4]([CH2:3][C:2]([C:37]2[CH:42]=[C:41]([CH3:43])[CH:40]=[C:39]([C:19]([CH3:21])([CH3:20])[CH3:18])[C:38]=2[OH:44])([CH3:45])[CH3:1])[C:9]1=[O:10]

Participants

Conditions

Temperature: 90 °C

Procedure

To a 50 ml 3-neck round bottom flask is charged 2 g product of Example 2 in 10 ml nitrobenzene. 0.1 ml H2SO4 is added and isobutylene is bubbled through the solution while warming to 90° C. After TLC shows the reaction to be complete, the mixture is diluted with an equal volume of ethyl acetate and washed 2 times with 50 ml 5% sodium bicarbonate. The organic layer is dried and concentrated in vacuo. The residue is purified by dry column chromatography (Et2O/hexane) to yield 1.3 g of product, mp 215°-217° C.

Workup

customisobutylene is bubbled through the solution
customthe reaction
washwashed 2 times with 50 ml 5% sodium bicarbonate
customThe organic layer is dried
concentrationconcentrated in vacuo
customThe residue is purified
dry with materialby dry column chromatography (Et2O/hexane)

Sources & evidence

ORD record: ord-d3b211d1d53c46a8b6a409bada275ac3
Source dataset: uspto-grants-1989_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04826983

Reaction notes

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