Acetic Acid → HCID 57075633, compound

HRID 2082623Notes

Reaction equation

HRID 2082623 reaction equation
[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH:27]([F:31])[CH:26]([CH3:32])[CH2:25][CH:24]([O:33][CH3:34])[CH:23]2[O:35][C:19]([OH:39])([CH:20]([CH3:38])[CH2:21][CH:22]2[O:36][CH3:37])[C:18](=[O:40])[C:17](=[O:41])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:42])[O:9][CH:8]([C:43]([CH3:56])=[CH:44][CH:45]2[CH2:50][CH2:49][CH:48]([N:51]=[N+:52]=[N-:53])[CH:47]([O:54][CH3:55])[CH2:46]2)[CH:7]([CH3:57])[CH:6]=[CH:5][C:4]1=[O:58])[CH3:2].C(O)(=O)C.C([SnH](CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH:27]([F:31])[CH:26]([CH3:32])[CH2:25][CH:24]([O:33][CH3:34])[CH:23]2[O:35][C:19]([OH:39])([CH:20]([CH3:38])[CH2:21][CH:22]2[O:36][CH3:37])[C:18](=[O:40])[C:17](=[O:41])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:42])[O:9][CH:8]([C:43]([CH3:56])=[CH:44][CH:45]2[CH2:50][CH2:49][CH:48]([N:51]=[N+:52]=[N-:53])[CH:47]([O:54][CH3:55])[CH2:46]2)[CH:7]([CH3:57])[CH2:6][CH2:5][C:4]1=[O:58])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5948TributylstannaneHCID 57176286HCID 57176286, compound

Product 1

HCID 57075633HCID 57075633, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 17-ethyl-20-fluoro-1-hydroxy-12-[2'-(4"-azido-3"-methoxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-14,18-diene-2, 3,10,16-tetraone (55 mg), tetrakistriphenylphosphine palladium (10 mg), and acetic acid (10 μl) in 3 ml of dry toluene is stirred for 5 min at room temperature under nitrogen atmosphere. To this yellow solution is added tributyltin hydride (30 μl) and stirred an additional 45 min at room temperature. The reaction mixture is subjected to column chromatography on silica gel (elute first with hexane and then with 50% ethyl acetate/hexane) to give the title compound.

Workup

  1. washelute first with hexane

Sources & evidence

ORD record
ord-576d83d3487e45d1964f6c8161ad0683
Source dataset
uspto-grants-1993_02
Patent number
US05189042

Reaction notes

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