(6Z,9Z,27Z,30Z)-19-hydroxyhexatriaconta-6,9,27,30-tetraen-18-yl 3-(dimethylamino)propanoate → (6Z,9Z,27Z,30Z)-19-hydroxyhexatriaconta-6,9,27,30-tetraen-18-yl 4-(dimethylamino)butanoate
Reaction equation
CN(C)CCC(OC(C(O)CCCCCCC/C=C\C/C=C\CCCCC)CCCCCCC/C=C\C/C=C\CCCCC)=O.[CH3:46][N:47]([CH3:91])[CH2:48][CH2:49][CH2:50][C:51]([O:53][CH:54]([CH:72]([OH:90])[CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH:80]=[CH:81][CH2:82][CH:83]=[CH:84][CH2:85][CH2:86][CH2:87][CH2:88][CH3:89])[CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH:62]=[CH:63][CH2:64][CH:65]=[CH:66][CH2:67][CH2:68][CH2:69][CH2:70][CH3:71])=[O:52]>>[CH3:91][N:47]([CH3:46])[CH2:48][CH2:49][CH2:50][C:51]([O:53][CH:54]([CH:72]([OH:90])[CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79]/[CH:80]=[CH:81]\[CH2:82]/[CH:83]=[CH:84]\[CH2:85][CH2:86][CH2:87][CH2:88][CH3:89])[CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61]/[CH:62]=[CH:63]\[CH2:64]/[CH:65]=[CH:66]\[CH2:67][CH2:68][CH2:69][CH2:70][CH3:71])=[O:52]Participants
3
Reactant 2
Product 1
Procedure
Using an analogous procedure to that described for the synthesis of (6Z,9Z,27Z,30Z)-19-hydroxyhexatriaconta-6,9,27,30-tetraen-18-yl 3-(dimethylamino)propanoate, 6Z,9Z,27Z,30Z)-19-hydroxyhexatriaconta-6,9,27,30-tetraen-18-yl 4-(dimethylamino)butanoate was obtained as a colorless oil (218 mg, 31%). 1H NMR (400 MHz, CDCl3): δ 5.44-5.29 (m, 8H), 4.92-4.81 (m, 1H), 3.71-3.54 (m, 1H), 2.81-2.75 (m, 4H), 2.46-2.34 (m, 1H), 2.28 (s, 3H), 2.27 (s, 3H), 2.09-2.02 (m, 8H), 1.94-1.78 (m, 2H), 1.69-1.20 (m, 36H), 0.93-0.86 (m, 6H).
Sources & evidence
- ORD record
- ord-aa1e64430635403d8c1ccb88981d7153
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08865675B2
Reaction notes
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