ethyl 4-{N-[4-(2-tetrahydropyranyloxy)nonyl]methanesulfonamido}butoxyacetate → 7-[N-(4(R)-hydroxy-2-nonynyl)methanesulfonamido]heptanoic acid

HRID 258609Notes

Reaction equation

HRID 258609 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7](C)[C:8]([O:10]CC)=[O:9].BrCCCCOCC(OCC)=O.O1CCCCC1[O:32][CH:33]([CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[CH2:34][CH2:35][CH2:36][N:37](CCCCOCC(OCC)=O)[S:38]([CH3:41])(=[O:40])=[O:39]>>[OH:32][C@H:33]([CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[C:34]#[C:35][CH2:36][N:37]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9])[S:38]([CH3:41])(=[O:40])=[O:39]

Participants

4

Reactant 3

HCID 20327707ethyl 4-{N-[4-(2-tetrahydropyranyloxy)nonyl]methanesulfonamido}butoxyacetateHCID 20436843Ethyl 2-(4-bromobutoxy)acetateHCID 22770549Ethyl 7-bromo-2-methylheptanoate

Product 1

HCID 227984047-[N-(4(R)-hydroxy-2-nonynyl)methanesulfonamido]heptanoic acid

Procedure

The synthesis of this compound is carried out as described in Example 8 except that, in Step A, the ethyl 7-bromo-2-methylheptanoate is replaced by an equimolar amount of ethyl 4-bromobutoxyacetate (Example M). The product of Step A is thus ethyl 4-{N-[4-(2-tetrahydropyranyloxy)nonyl]methanesulfonamido}butoxyacetate. The subsequent step yields 4-[N-(4-hydroxynonyl)methanesulfonamido]butoxyacetic acid (B).

Workup

  1. customThe synthesis of this compound

Sources & evidence

ORD record
ord-0a20112412f746a780939a517870c513
Source dataset
uspto-grants-1977_07
Patent number
US04033996

Reaction notes

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