1-Nonanol, 9-bromo- → HCID 66875175, compound

HRID 1799660Notes

Reaction equation

HRID 1799660 reaction equation
[Na+].C1(S([O-])=O)C=CC=CC=1.BrCCCCCCCCCO.[C:22]1([S:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][OH:40])(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(S(CCCCCCCCC(O)=O)(=O)=O)C=CC=CC=1.Cl.Cl.[CH2:63]([O:70][C:71](=[O:79])[CH2:72][C@@H:73]([NH2:78])[CH2:74][N:75]([CH3:77])[CH3:76])[C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1>>[CH2:63]([O:70][C:71](=[O:79])[CH2:72][C@@H:73]([NH:78][C:39](=[O:40])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][S:28]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)(=[O:29])=[O:30])[CH2:74][N:75]([CH3:76])[CH3:77])[C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1

Participants

6

Reactant 5

HCID 1087001-Nonanol, 9-bromo-HCID 2723840Benzenesulfinic acid, sodium saltHCID 114929471-Nonanol, 9-(phenylsulfonyl)-HCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochlorideHCID 58352734HCID 58352734, compound

Product 1

HCID 66875175HCID 66875175, compound

Procedure

The title compound, m/e=427.5 ([M+H]+), was produced in analogy with example 18, steps 1 to 4. Thus, benzenesulfinic acid sodium salt was alkylated in step 1 with 9-bromo-1-nonanol, leading to 9-benzenesulfonyl-nonan-1-ol, which was oxidized in step 2 to 9-benzenesulfonyl-nonanoic acid. This was coupled in step 3 with (R)-3-amino-4-dimethylamino-butyric acid benzyl ester dihydrochloride to produce (R)-3-(9-benzenesulfonyl-nonanoylamino)-4-dimethylamino-butyric acid benzyl ester, which was hydrogenated in step 4.

Sources & evidence

ORD record
ord-653604d9e30541fca205b83d82c4c289
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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