Methyl 4-pentynoate → HCID 11742322, compound

HRID 1938935Notes

Reaction equation

HRID 1938935 reaction equation
[CH2:1]([C:3]1(O)[CH:27]=[C:26]2[C@:21]([CH3:29])([CH2:22][CH2:23][C@H:24]([OH:28])[CH2:25]2)[C@@H:20]2[C@@H:4]1[C@H:5]1[C@:17]([CH3:30])([CH2:18][CH2:19]2)[C@@H:8]([C@H:9]([CH3:16])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:7][CH2:6]1)[CH3:2].C(OC)(=O)CCC#C>[Pd]>[CH2:1]([C:3]1[C@@H:4]2[C@@H:20]([C@:21]3([CH3:29])[C:26]([CH:27]=1)=[CH:25][C:24](=[O:28])[CH2:23][CH2:22]3)[CH2:19][CH2:18][C@@:17]1([CH3:30])[C@H:5]2[CH2:6][CH2:7][C@@H:8]1[C@H:9]([CH3:16])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[CH3:2]

Participants

4

Reactant 2

HCID 543061Methyl 4-pentynoateHCID 57243272HCID 57243272, compound

Product 1

HCID 11742322HCID 11742322, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The synthesis of the acid 41 and 65 is published in J. Med. Chem. 1986 Vol. 29, p. 2300. The acids 45, 63, and 64 were prepared by the reaction sequence detailed in Example 226. Palladium catalyzed coupling of the Δ16 -17-triflate 60 with methyl 4-pentynoate using the procedures published in Synlett. 1991 p. 409; J. Org. Chem. 1992 Vol. 57, p. 973. gave the enyne 61. Hydrogenation catalyzed with palladium on carbon formed the saturated ester 62 and KOH saponification gave 45. Similar reaction sequences using methyl 5-hexynoate and 10-undecynoic acid gave the acids 63 and 64.

Workup

  1. customThe acids 45, 63, and 64 were prepared by the reaction sequence

Sources & evidence

ORD record
ord-54f252a745844cd8a6f432db0e57c877
Source dataset
uspto-grants-1997_12
Patent number
US05693809

Reaction notes

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