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

HRID 2205032Notes

Reaction equation

HRID 2205032 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@@H:19]([CH2:27][S:28][CH2:29][C@H:30]([OH:33])[CH2:31][OH:32])[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:34](Cl)(=[O:48])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47].C(OC[C@@H](OC(=O)CCCCCCCCCCC)CSC[C@H](NC([O:80][CH2:81][CH:82]1[C:94]2[CH:93]=[CH:92][CH:91]=[CH:90][C:89]=2[C:88]2[C:83]1=[CH:84][CH:85]=[CH:86][CH:87]=2)=O)C(OC(C)(C)C)=O)(=O)CCCCCCCCCCC>>[C:34]([O:32][CH2:31][C@@H:30]([O:33][C:81](=[O:80])[CH2:82][CH2:83][CH2:84][CH2:85][CH2:86][CH2:87][CH2:88][CH2:89][CH2:94][CH2:93][CH2:92][CH2:91][CH3:90])[CH2:29][S:28][CH2:27][C@H:19]([NH:18][C:16]([O:15][CH2:14][CH:12]1[C:13]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:17])[C:20]([O:22][C:23]([CH3:26])([CH3:24])[CH3:25])=[O:21])(=[O:48])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47]

Participants

4

Reactant 3

HCID 66986Myristoyl 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 10440751(R)-3-((R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-tert-butoxy-3-oxopropylthio)propane-1,2-diyl ditetradecanoate

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

Sources & evidence

ORD record
ord-e20fef8376eb43c6a77ab87544cd2813
Source dataset
uspto-grants-2016_06
Patent number
US09365506B2

Reaction notes

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