Methyl formate → HCID 74990286, compound

HRID 248236Notes

Reaction equation

HRID 248236 reaction equation
[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH2:27][CH:26]([CH3:31])[CH2:25][CH:24]([O:32][CH3:33])[CH:23]2[O:34][C:19]([OH:38])([CH:20]([CH3:37])[CH2:21][CH:22]2[O:35][CH3:36])[C:18](=[O:39])[C:17](=[O:40])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:41])[O:9][CH:8]([C:42]([CH3:53])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([NH2:50])[CH:46]([O:51][CH3:52])[CH2:45]2)[CH:7]([CH3:54])[CH:6]([OH:55])[CH2:5][C:4]1=[O:56])[CH3:2].[CH:57](OC)=[O:58]>>[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH2:27][CH:26]([CH3:31])[CH2:25][CH:24]([O:32][CH3:33])[CH:23]2[O:34][C:19]([OH:38])([CH:20]([CH3:37])[CH2:21][CH:22]2[O:35][CH3:36])[C:18](=[O:39])[C:17](=[O:40])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:41])[O:9][CH:8]([C:42]([CH3:53])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([NH:50][CH:57]=[O:58])[CH:46]([O:51][CH3:52])[CH2:45]2)[CH:7]([CH3:54])[CH:6]([OH:55])[CH2:5][C:4]1=[O:56])[CH3:2]

Participants

3

Reactant 2

HCID 7865Methyl formateHCID 57322588HCID 57322588, compound

Product 1

HCID 74990286HCID 74990286, compound

Conditions

Temperature
0 °C

Procedure

The compound 17-ethyl-1,14-dihydroxy-12-[2'-(4"-amino-3"-methoxycyclohexyl)-1'-methylvinyl]-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 (30 mg) was mixed with methyl formate (0.5 ml) and stirred at 0° C. for 1 hr. The reaction mixture was allowed to warm to room temperature and then stirred overnight. The excess methylformate was removed with nitrogen flow and the crude mixture was purified by preparative tlc on silica gel (1000 microns, 5% i-PrOH/CH2Cl2) to give 25 mg of the title compound. (Mass, 1H and 13C data were consistent with the proposed structure).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. customThe excess methylformate was removed with nitrogen flow
  4. customthe crude mixture was purified by preparative tlc on silica gel (1000 microns, 5% i-PrOH/CH2Cl2)

Sources & evidence

ORD record
ord-26366f0fafde40e1b9ed48dd56e35c58
Source dataset
uspto-grants-1993_05
Patent number
US05208228

Reaction notes

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