1-Bromo-4-acetoxy-4-propyl-2-heptyne → 7-{N-[3(1-hydroxycyclooctyl)propyl]methanesulfonamido}heptanoic acid

HRID 372536Notes

Reaction equation

HRID 372536 reaction equation
Br[CH2:2][C:3]#[C:4][C@H:5]([O:11][C:12](=[O:14])[CH3:13])[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].Br[CH2:16][C:17]#CC(OC(=O)C)(CCC)CCC.C([O:33][C:34]([CH2:57][CH2:58][CH3:59])([CH2:54][CH2:55][CH3:56])[C:35]#[C:36][CH2:37][N:38]([CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][C:49]([O:51]CC)=[O:50])[S:39]([CH3:42])(=[O:41])=[O:40])(=O)C>>[CH2:16]([CH:48]([CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][N:38]([CH2:2]/[CH:3]=[CH:4]/[CH:5]([O:11][C:12](=[O:14])[CH3:13])[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[S:39]([CH3:42])(=[O:40])=[O:41])[C:49]([OH:51])=[O:50])[CH3:17].[OH:33][C:34]1([CH2:35][CH2:36][CH2:37][N:38]([CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][C:49]([OH:51])=[O:50])[S:39]([CH3:42])(=[O:40])=[O:41])[CH2:54][CH2:55][CH2:56][CH2:2][CH2:59][CH2:58][CH2:57]1

Participants

5

Reactant 3

HCID 203277141-Bromo-4-acetoxy-4-propyl-2-heptyneHCID 20327720ethyl 7-[N-(4-acetoxy-4-propyl-2-heptynyl)methanesulfonamido]heptanoateHCID 227938161-bromo-4(R)-acetoxy-2-nonyne

Product 2

HCID 203276917-{N-[3(1-hydroxycyclooctyl)propyl]methanesulfonamido}heptanoic acidHCID 20327696ethyl 7-[N-(4-acetoxy-(E)-2-nonenyl)methanesulfonamido]heptanoic acid

Procedure

The synthesis of this compound is carried out as described in Example 3, except that, in Step A, the 1-bromo-4(R)-acetoxy-2-nonyne is replaced by an equimolar amount of 1-bromo-4-acetoxy-4-propyl-2-heptyne (Example W). The product of Step A is thus ethyl 7-[N-(4-acetoxy-4-propyl-2-heptynyl)methanesulfonamido]heptanoate. The subsequent steps yield 7-[N-(4-hydroxy-4-propyl-2-heptynyl)methanesulfonamido]heptanoic acid (B) and 7-[N-(4-hydroxy-4-propylhexyl)methanesulfonamido]heptanoic acid (C).

Workup

  1. customThe synthesis of this compound

Sources & evidence

ORD record
ord-df40306d614e4d2896361f0233029162
Source dataset
uspto-grants-1978_05
Patent number
US04091107

Reaction notes

Loading…