Methyl 7-iodo-2,2-dimethylheptanoate → 7-[1-(4(R)-hydroxy-2-nonynyl)ureido]heptanoic acid

HRID 1729919Notes

Reaction equation

HRID 1729919 reaction equation
BrCCCCCC(C)C(OCC)=[O:9].CC(C)(CCCCCI)C(OC)=O.C([O:30][CH:31]([CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[CH2:32][CH2:33][CH2:34][N:35]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43](C)(C)[C:44]([O:46]C)=[O:45])[C:36]#[N:37])(=O)C>>[OH:30][C@H:31]([CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[C:32]#[C:33][CH2:34][N:35]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44]([OH:46])=[O:45])[C:36]#[N:37].[OH:30][C@H:31]([CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[C:32]#[C:33][CH2:34][N:35]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44]([OH:46])=[O:45])[C:36]([NH2:37])=[O:9]

Participants

5

Reactant 3

HCID 14153168Methyl 7-iodo-2,2-dimethylheptanoateHCID 22770549Ethyl 7-bromo-2-methylheptanoateHCID 86734145methyl 7-[N-(4-acetoxynonyl)cyanamido]-2,2-dimethylheptanoate

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 2,2-dimethyl-7-iodoheptanoate. The product of Step A is thus methyl 7-[N-(4-acetoxynonyl)cyanamido]-2,2-dimethylheptanoate. The subsequent steps yield 7-[N-(4-hydroxynonyl)cyanamido]-2,2-dimethylheptanoic acid (B) and 7-[1-(4-hydroxynonyl)ureido]-2,2-dimethylheptanoic acid (C).

Workup

  1. customThe synthesis of this compound

Sources & evidence

ORD record
ord-1058e0a4eb224dfa9473be23d80a6be5
Source dataset
uspto-grants-1976_11
Patent number
US03989749

Reaction notes

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