Diazomethane → HCID 57261554, compound

HRID 1492951Notes

Reaction equation

HRID 1492951 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]([CH3:54])=[CH:44][CH:45]2[CH2:50][CH2:49][CH:48]([OH:51])[CH:47](OC)[CH2:46]2)[CH:8]([CH3:55])[CH:7]=[CH:6][C:5]1=[O:56])[CH:2]=[CH2:3].[N+](=C)=[N-].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.B(F)(F)F.CCOCC.C(OCC)C>[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]([CH3:54])=[CH:44][CH:45]2[CH2:50][CH2:49][CH:48]3[O:51][CH:47]3[CH2:46]2)[CH:8]([CH3:55])[CH:7]=[CH:6][C:5]1=[O:56])[CH:2]=[CH2:3]

Participants

7

Reactant 3

HCID 9550DiazomethaneHCID 10340Sodium CarbonateHCID 5715345717-Allyl-1-hydroxy-12-[2-(4-hydroxy-3-methoxycyclohexyl)-1-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacosa-14,18-diene-2,3,10,16-tetraone

Product 1

HCID 57261554HCID 57261554, compoundYield 5.7%

Reagents, catalysts & solvents 3

HCID 8000Boron trifluoride etherateCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the title compound of Example 14 (823 mg, 1.05 mmole) in dry dichloromethane (50 ml) was added boron trifluoride diethyl etherate (1 drop) followed by portionwise addition of a dried solution of diazomethane in diethyl ether until no starting material remained. Sodium carbonate was then added, and the resulting mixture stirred for 30 minutes at room temperature. The reaction mixture was then filtered, concentrated in vacuo, and chromatographed on silica eluting with 40°-60° petroleum ether/ethyl acetate [3:1] to give the title compound as an oil (45 mg).

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationconcentrated in vacuo
  3. customchromatographed on silica eluting with 40°-60° petroleum ether/ethyl acetate [3:1]

Sources & evidence

ORD record
ord-88bb936c31d940818674d701ea3db251
Source dataset
uspto-grants-1994_12
Patent number
US05376663

Reaction notes

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