Methyl 3-methyl-7-iodoheptanoate → 7-[1-(4(R)-hydroxy-2-nonynyl)ureido]heptanoic acid

HRID 1729920Notes

Reaction equation

HRID 1729920 reaction equation
BrCCCCCC(C)C(OCC)=[O:9].CC(CCCCI)CC(OC)=O.C([O:29][CH:30]([CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])[CH2:31][CH2:32][CH2:33][N:34]([CH2:37][CH2:38][CH2:39][CH2:40][CH:41](C)[CH2:42][C:43]([O:45]C)=[O:44])[C:35]#[N:36])(=O)C>>[OH:29][C@H:30]([CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])[C:31]#[C:32][CH2:33][N:34]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43]([OH:45])=[O:44])[C:35]#[N:36].[OH:29][C@H:30]([CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])[C:31]#[C:32][CH2:33][N:34]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43]([OH:45])=[O:44])[C:35]([NH2:36])=[O:9]

Participants

5

Reactant 3

HCID 20322201Methyl 3-methyl-7-iodoheptanoateHCID 22770549Ethyl 7-bromo-2-methylheptanoateHCID 86734146methyl 7-[N-(4-acetoxynonyl)cyanamido]-3-methylheptanoate

Product 2

HCID 227942327-[1-(4(R)-hydroxy-2-nonynyl)ureido]heptanoic acidHCID 867341417-[N-(4-(R)-hydroxy-2-nonynyl)cyanamido]heptanoic acid

Procedure

The synthesis of this compound is carried out as described in Example 7 except that, in Step A, the ethyl 7-bromo-2-methylheptanoate is replaced by an equimolar amount of methyl 3-methyl-7-iodoheptanoate. The product of Step A is thus methyl 7-[N-(4-acetoxynonyl)cyanamido]-3-methylheptanoate. The subsequent steps yield 7-[N-(4-hydroxynonyl)cyanamido]-3-methylheptanoic acid (B) and 7-[1-(4-hydroxynonyl)ureido]-2-methylheptanoic acid (C).

Workup

  1. customThe synthesis of this compound

Sources & evidence

ORD record
ord-eb76f882de1847ebb7f271eeef2b7e50
Source dataset
uspto-grants-1976_11
Patent number
US03989749

Reaction notes

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