HCID 15063013, compound → HCID 57548711, compound

HRID 1367720Notes

Reaction equation

I[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].[I:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30]Br)=[CH:25][CH:24]=1>>[I:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:25][CH:24]=1

Participants

Reactant 2

HCID 15063013HCID 15063013, compound

HCID 221164171-(2-Bromoethyl)-4-iodobenzene

Product 1

HCID 57548711HCID 57548711, compound

Procedure

Another approach is shown in SCHEME III. It can be described as C16+IPhC2=IPhC18. The C16 fragment 43 originates from relatively inexpensive 16-hexadecanolactone 31. Lactone cleavage with trimethylsilyl iodide in the presence of ethanol results in ethyl 16-iodohexadecanoate 43. Iodoester 43 is coupled with organozinc reagent 44 made from 2-(p-iodophenyl)ethyl bromide to give ester 37 which has all 18 carbons chain required for NM404. Ester 37 is converted into 18-(p-iodophenyl)octadecanol 12 in two steps as shown in SCHEME III.

Sources & evidence

ORD record: ord-1eaf798b226b4e4c8dac53d93bb90899
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893286B2

Reaction notes

Loading…