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

HRID 2205026Notes

Reaction equation

HRID 2205026 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)CCCCCCC.[C:44]([O:57][CH2:58][C@@H:59]([O:89][C:90](=[O:102])[CH2:91][CH2:92][CH2:93][CH2:94][CH2:95][CH2:96][CH2:97]CCCC)[CH2:60][S:61][CH2:62][C@H:63]([NH:71][C:72]([O:74][CH2:75][CH:76]1[C:88]2[CH:87]=[CH:86][CH:85]=[CH:84][C:83]=2[C:82]2[C:77]1=[CH:78][CH:79]=[CH:80][CH:81]=2)=[O:73])[C:64]([O:66][C:67]([CH3:70])([CH3:69])[CH3:68])=[O:65])(=[O:56])[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51]CCCC>>[C:44]([O:57][CH2:58][C@@H:59]([O:89][C:90](=[O:102])[CH2:91][CH2:92][CH2:93][CH2:94][CH2:95][CH2:96][CH3:97])[CH2:60][S:61][CH2:62][C@H:63]([NH:71][C:72]([O:74][CH2:75][CH:76]1[C:88]2[CH:87]=[CH:86][CH:85]=[CH:84][C:83]=2[C:82]2[C:77]1=[CH:78][CH:79]=[CH:80][CH:81]=2)=[O:73])[C:64]([O:66][C:67]([CH3:68])([CH3:70])[CH3:69])=[O:65])(=[O:56])[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51]

Participants

4

Reactant 3

HCID 8124Octanoyl 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 67400188(R)-3-((R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-tert-butoxy-3-oxopropylthio)propane-1,2-diyl dioctanoate

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 octanoyl chloride (3.7 eq) by following the procedure described for compound 11.

Sources & evidence

ORD record
ord-a0ee6809ea084ac8b60d3f214c7cb5f8
Source dataset
uspto-grants-2016_06
Patent number
US09365506B2

Reaction notes

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