Ethyl 7-bromoheptanoate → ethyl 7-[N-(4-acetoxynonyl)-acrylamido]heptanoate

HRID 1288349Notes

Reaction equation

HRID 1288349 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].CC(CCCCI)CC(OC)=[O:17].[O:25]1CCC[CH2:27][CH:26]1[O:31][CH:32]([CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[CH2:33][CH2:34][CH2:35][N:36]([CH2:40][CH2:41][CH2:42]CC(C)CC(OC)=O)C(=O)C>>[C:26]([O:31][CH:32]([CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[CH2:33][CH2:34][CH2:35][N:36]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:40](=[O:17])[CH:41]=[CH2:42])(=[O:25])[CH3:27]

Participants

4

Reactant 3

HCID 122490Ethyl 7-bromoheptanoateHCID 20322201Methyl 3-methyl-7-iodoheptanoateHCID 21503938methyl 7-{N-[4-(2-tetrahydropyranyloxy)nonyl]acetamido}-3-methylheptanoate

Product 1

HCID 21503957ethyl 7-[N-(4-acetoxynonyl)-acrylamido]heptanoate

Procedure

The synthesis of this compound is carried out as described in Example 1 except that, in Step A, the ethyl 7-bromoheptanoate is replaced by an equimolar amount of methyl 3-methyl-7-iodoheptanoate. The product of Step A is methyl 7-{N-[4-(2-tetrahydropyranyloxy)nonyl]acetamido}-3-methylheptanoate. The subsequent step yields 7-[N-(4-hydroxynonyl)acetamido]-3-methylheptanoic acid (B).

Workup

  1. customThe synthesis of this compound

Sources & evidence

ORD record
ord-47b6dc8f0c66480091909132558d028b
Source dataset
uspto-grants-1976_10
Patent number
US03987091

Reaction notes

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