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

HRID 258607Notes

Reaction equation

HRID 258607 reaction equation
BrCCCCCC(C)C(OCC)=O.CC(C)(CCCCCI)C(OC)=O.O1CCCCC1[O:33][CH:34]([CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])[CH2:35][CH2:36][CH2:37][N:38]([CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][C:48](C)(C)[C:49]([O:51]C)=[O:50])[S:39]([CH3:42])(=[O:41])=[O:40]>>[OH:33][C@H:34]([CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])[C:35]#[C:36][CH2:37][N:38]([CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][C:49]([OH:51])=[O:50])[S:39]([CH3:42])(=[O:40])=[O:41]

Participants

4

Reactant 3

HCID 14153168Methyl 7-iodo-2,2-dimethylheptanoateHCID 20327676methyl 7-{N-[4-(2-tetrahydropyranyloxy)nonyl]methanesulfonamido}-2,2-dimethylheptanoateHCID 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 2,2-dimethyl-7-iodoheptanoate. The product of Step A is thus methyl 7-{N-[4-(2-tetrahydropyranyloxy)nonyl]methanesulfonamido}-2,2-dimethylheptanoate. The subsequent step yields 7-[N-(4-hydroxynonyl)methanesulfonamido]-2,2-dimethylheptanoic acid (B).

Workup

  1. customThe synthesis of this compound

Sources & evidence

ORD record
ord-5efc89deb0fe48d4b7e979fd8d31adc8
Source dataset
uspto-grants-1977_07
Patent number
US04033996

Reaction notes

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