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

HRID 1288350Notes

Reaction equation

HRID 1288350 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(C)(CCCCCI)C(OC)=[O:16].[O:26]1CCC[CH2:28][CH:27]1[O:32][CH:33]([CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[CH2:34][CH2:35][CH2:36][N:37]([CH2:41][CH2:42][CH2:43]CCC(C)(C)C(OC)=O)C(=O)C>>[C:27]([O:32][CH:33]([CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[CH2:34][CH2:35][CH2:36][N:37]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:41](=[O:16])[CH:42]=[CH2:43])(=[O:26])[CH3:28]

Participants

4

Reactant 3

HCID 122490Ethyl 7-bromoheptanoateHCID 14153168Methyl 7-iodo-2,2-dimethylheptanoateHCID 21503971methyl 7-{N-[4-(2-tetrahydropyranyloxy)nonyl]-acetamido}-2,2-dimethylheptanoate

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 2,2-dimethyl-7-iodoheptanoate. The product of Step A is methyl 7-{N-[4-(2-tetrahydropyranyloxy)nonyl]-acetamido}-2,2-dimethylheptanoate. The subsequent step yields 7-[N-(4-hydroxynonyl)acetamido]-2,2-dimethylheptanoic acid (B).

Workup

  1. customThe synthesis of this compound

Sources & evidence

ORD record
ord-37a4701102e7422ab8970f35d67fb069
Source dataset
uspto-grants-1976_10
Patent number
US03987091

Reaction notes

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