Methyl-9-trityloxy-nonanoate → Dodecanoic acid, 12-(triphenylmethoxy)-

HRID 467393

Reaction equation

HRID 467393 reaction equation
C(OCCCCCC(OC)=O)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.COC(=O)CCCCCCCCOC(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C[O:63][C:64](=[O:96])[CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][O:76][C:77]([C:90]1[CH:95]=[CH:94][CH:93]=[CH:92][CH:91]=1)([C:84]1[CH:89]=[CH:88][CH:87]=[CH:86][CH:85]=1)[C:78]1[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=1>>[C:77]([O:76][CH2:75][CH2:74][CH2:73][CH2:72][CH2:71][CH2:70][CH2:69][CH2:68][CH2:67][CH2:66][CH2:65][C:64]([OH:96])=[O:63])([C:84]1[CH:85]=[CH:86][CH:87]=[CH:88][CH:89]=1)([C:90]1[CH:95]=[CH:94][CH:93]=[CH:92][CH:91]=1)[C:78]1[CH:79]=[CH:80][CH:81]=[CH:82][CH:83]=1

Participants

4

Reactant 3

HCID 42624366Methyl-9-trityloxy-nonanoateHCID 67198977Methyl 6-trityloxy-hexanoateHCID 67200799Methyl-12-trityloxy-dodecanoate

Product 1

HCID 10790077Dodecanoic acid, 12-(triphenylmethoxy)-

Procedure

Hydrolysis of the methyl ester of 15a, 15b, and 15c was carried out under basic conditions, followed by an acidic work up, during which the pH was maintained above 4 to prevent trityl deprotection. After recrystallization for solid product or flash chromatography for oil products, 6-trityloxyhexanoic acid 16a, 9-trityloxynonanoic acid 16b and 12-trityloxydodecanoic acid 16c were isolated, providing aliphatic side-chains that were ready to be coupled to 12 and 13.

Workup

  1. temperatureduring which the pH was maintained above 4
  2. customAfter recrystallization for solid product or flash chromatography for oil products, 6-trityloxyhexanoic acid 16a, 9-trityloxynonanoic acid 16b

Sources & evidence

ORD record
ord-0c3f2de7ecae4ff483c3d51b7ba30cc8
Source dataset
uspto-grants-2014_01
Patent number
US08623326B2

Linked notes

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