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

HRID 258608Notes

Reaction equation

HRID 258608 reaction equation
BrCCCCCC(C)C(OCC)=O.CC(CCCCI)CC(OC)=O.O1CCCCC1[O:32][CH:33]([CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[CH2:34][CH2:35][CH2:36][N:37]([CH2:42][CH2:43][CH2:44][CH2:45][CH:46](C)[CH2:47][C:48]([O:50]C)=[O:49])[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]([CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][C:48]([OH:50])=[O:49])[S:38]([CH3:41])(=[O:39])=[O:40]

Participants

4

Reactant 3

HCID 20322201Methyl 3-methyl-7-iodoheptanoateHCID 20327668methyl 7-{N-[4-(2-tetrahydropyranyloxy)nonyl]methanesulfonamido}-3-methylheptanoateHCID 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 methyl 3-methyl-7-iodoheptanoate. The product of Step A is thus methyl 7-{N-[4-(2-tetrahydropyranyloxy)nonyl]methanesulfonamido}-3-methyl-heptanoate. The subsequent hydrolysis step yields 7-[N-(4-hydroxynonyl)methanesulfonamido]-3-methylheptanoic acid (B).

Workup

  1. customThe synthesis of this compound
  2. customThe subsequent hydrolysis step

Sources & evidence

ORD record
ord-590e26dd14694cc49748b28066e09822
Source dataset
uspto-grants-1977_07
Patent number
US04033996

Reaction notes

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