1-Chloro-4-acetoxynonane → 7-[N-(4(R)-hydroxy-2-nonynyl)acetamido]heptanoic acid

HRID 1288355Notes

Reaction equation

HRID 1288355 reaction equation
ClCCCC(OC(=O)C)CCCCC.ClCCCC(OC(=O)C)C(C)(C)CCCC.C([O:34][CH:35]([C:54](C)(C)[CH2:55][CH2:56][CH2:57][CH3:58])[CH2:36][CH2:37][CH2:38][N:39]([CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][C:49]([O:51]CC)=[O:50])[C:40](=[O:42])[CH3:41])(=O)C>>[OH:34][C@H:35]([CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[C:36]#[C:37][CH2:38][N:39]([CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][C:49]([OH:51])=[O:50])[C:40](=[O:42])[CH3:41]

Participants

4

Reactant 3

HCID 131047161-Chloro-4-acetoxynonaneHCID 203861071-Chloro-4-acetoxy-5,5-dimethylnonaneHCID 21503963ethyl 7-[N-(4-acetoxy-5,5-dimethylnonyl)acetamido]heptanoate

Product 1

HCID 227938207-[N-(4(R)-hydroxy-2-nonynyl)acetamido]heptanoic acid

Procedure

The synthesis of this compound is carried out as described in Example 2 except that, in Step B, the 1-chloro-4-acetoxynonane is replaced by an equimolar amount of 1-chloro-4-acetoxy-5,5-dimethylnonane (Example G, Step 3). The product in Step B is ethyl 7-[N-(4-acetoxy-5,5-dimethylnonyl)acetamido]heptanoate. The subsequent step yields 7-[N-(4-hydroxy-5,5-dimethylnonyl)acetamido]-heptanoic acid (C).

Workup

  1. customThe synthesis of this compound

Sources & evidence

ORD record
ord-1d48e0ae950247b084e1a775ec8a1bb6
Source dataset
uspto-grants-1976_10
Patent number
US03987091

Reaction notes

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