Decanoyl chloride → (R)-3-((R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-tert-butoxy-3-oxopropylthio)propane-1,2-diyl bis(decanoate)

HRID 2205029Notes

Reaction equation

HRID 2205029 reaction equation
C1C2C(COC(N[C@@H](CSC[C@H](O)CO)C(OC(C)(C)C)=O)=O)C3C(=CC=CC=3)C=2C=CC=1.C(Cl)(=O)CCCCCCCCC.[C:46]([O:59][CH2:60][C@@H:61]([O:91][C:92](=[O:104])[CH2:93][CH2:94][CH2:95][CH2:96][CH2:97][CH2:98][CH2:99][CH2:100][CH2:101]CC)[CH2:62][S:63][CH2:64][C@H:65]([NH:73][C:74]([O:76][CH2:77][CH:78]1[C:90]2[CH:89]=[CH:88][CH:87]=[CH:86][C:85]=2[C:84]2[C:79]1=[CH:80][CH:81]=[CH:82][CH:83]=2)=[O:75])[C:66]([O:68][C:69]([CH3:72])([CH3:71])[CH3:70])=[O:67])(=[O:58])[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55]CC>>[C:46]([O:59][CH2:60][C@@H:61]([O:91][C:92](=[O:104])[CH2:93][CH2:94][CH2:95][CH2:96][CH2:97][CH2:98][CH2:99][CH2:100][CH3:101])[CH2:62][S:63][CH2:64][C@H:65]([NH:73][C:74]([O:76][CH2:77][CH:78]1[C:79]2[CH:80]=[CH:81][CH:82]=[CH:83][C:84]=2[C:85]2[C:90]1=[CH:89][CH:88]=[CH:87][CH:86]=2)=[O:75])[C:66]([O:68][C:69]([CH3:70])([CH3:72])[CH3:71])=[O:67])(=[O:58])[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55]

Participants

4

Reactant 3

HCID 66982Decanoyl chlorideHCID 10412572(R)-tert-butyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-((R)-2,3-dihydroxypropylthio)propanoateHCID 66613539(R)-3-((R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-tert-butoxy-3-oxopropylthio)propane-1,2-diyl didodecanoate

Product 1

HCID 67402798(R)-3-((R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-tert-butoxy-3-oxopropylthio)propane-1,2-diyl bis(decanoate)

Procedure

The product was prepared from (R)-tert-butyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-((R)-2,3-dihydroxypropylthio)propanoate (10, 1 eq) and decanoyl chloride (3.7 eq) by following the procedure described for compound 11.

Sources & evidence

ORD record
ord-3e5d7566d469448a827e57a49fc3e0c0
Source dataset
uspto-grants-2016_06
Patent number
US09365506B2

Reaction notes

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