1-Acetoxy-1-(3-bromo-1-propynyl)cyclooctane → 7-{N-[3(1-hydroxycyclooctyl)propyl]methanesulfonamido}heptanoic acid

HRID 258622Notes

Reaction equation

HRID 258622 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].[C:15]([O:18][C:19]1([C:27]#[C:28][CH2:29]Br)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)(=O)[CH3:16].C(OC1(C#CC[CH2:46][S:47]([NH:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][C:57]([O:59]CC)=[O:58])(=[O:49])=[O:48])CCCCCCC1)(=O)C>>[CH2:15]([CH:56]([CH2:55][CH2:54][CH2:53][CH2:52][CH2:51][N:50]([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:47]([CH3:46])(=[O:48])=[O:49])[C:57]([OH:59])=[O:58])[CH3:16].[OH:18][C:19]1([CH2:27][CH2:28][CH2:29][N:50]([CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][C:57]([OH:59])=[O:58])[S:47]([CH3:46])(=[O:49])=[O:48])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

5

Reactant 3

HCID 203222401-Acetoxy-1-(3-bromo-1-propynyl)cyclooctaneHCID 20327721Ethyl 7-{[3-(1-acetoxycyclooctyl)-2-propynyl]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-acetoxy-1-(3-bromo-1-propynyl)cyclooctane (Example V). The product of Step A is thus ethyl 7-{[3-(1-acetoxycyclooctyl)-2-propynyl]methanesulfonamido}heptanoate. The subsequent steps yield 7-{N-[3-(1-hydroxycyclooctyl)-2-propynyl]methanesulfonamido}heptanoic acid (B) and 7-{N-[3(1-hydroxycyclooctyl)propyl]methanesulfonamido}heptanoic acid (C).

Workup

  1. customThe synthesis of this compound

Sources & evidence

ORD record
ord-f76e47127b6f4d47b89046b4103d4898
Source dataset
uspto-grants-1977_07
Patent number
US04033996

Reaction notes

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