Hexylene Glycol → Temsirolimus

HRID 1437796

Reaction equation

HRID 1437796 reaction equation
[CH3:1][C@H:2]1[C@@:41]2([OH:43])[O:42][C@H:5]([CH2:6][C@H:7]([O:72][CH3:73])[C:8]([CH3:71])=[CH:9][CH:10]=[CH:11][CH:12]=[CH:13][C@@H:14]([CH3:70])[CH2:15][C@@H:16]([CH3:69])[C:17]([C@H:19]([O:67][CH3:68])[C@H:20]([OH:66])[C:21]([CH3:65])=[CH:22][C@@H:23]([CH3:64])[C:24]([CH2:26][C@@H:27]([C@@H:44]([CH2:46][C@H:47]3[CH2:52][C@@H:51]([O:53][CH3:54])[C@H:50]([O:55][C:56]([C:58]([CH2:62][OH:63])([CH2:60][OH:61])[CH3:59])=[O:57])[CH2:49][CH2:48]3)[CH3:45])[O:28][C:29]([C@H:31]3[N:36]([C:37]([C:39]2=[O:40])=[O:38])[CH2:35][CH2:34][CH2:33][CH2:32]3)=[O:30])=[O:25])=[O:18])[CH2:4][CH2:3]1.B([O-])[O-].CC(O)(CC(O)C)C>CCOCC>[CH3:1][C@H:2]1[C@@:41]2([OH:43])[O:42][C@H:5]([CH2:6][C@H:7]([O:72][CH3:73])[C:8]([CH3:71])=[CH:9][CH:10]=[CH:11][CH:12]=[CH:13][C@@H:14]([CH3:70])[CH2:15][C@@H:16]([CH3:69])[C:17]([C@H:19]([O:67][CH3:68])[C@H:20]([OH:66])[C:21]([CH3:65])=[CH:22][C@@H:23]([CH3:64])[C:24]([CH2:26][C@@H:27]([C@@H:44]([CH2:46][C@H:47]3[CH2:52][C@@H:51]([O:53][CH3:54])[C@H:50]([O:55][C:56]([C:58]([CH2:60][OH:61])([CH2:62][OH:63])[CH3:59])=[O:57])[CH2:49][CH2:48]3)[CH3:45])[O:28][C:29]([C@H:31]3[N:36]([C:37]([C:39]2=[O:40])=[O:38])[CH2:35][CH2:34][CH2:33][CH2:32]3)=[O:30])=[O:25])=[O:18])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 7870Hexylene GlycolHCID 178496632HCID 178496632, compound

Product 1

HCID 6918289Temsirolimus

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Crude CCI-779 was prepared essentially as described above from CCI-779 boronate using 5 eq. of 2-methyl-2,4-pentanediol in a mixture of ether and heptanes (2:1, Wt/Wt) at 34° C. for 6 hours. The crude CCI-779 was isolated by filtration. The crude CCI-779 was suspended in ether, then treated with 5 eq. of 2-methyl-2,4-pentanediol, following by addition of heptanes, filtration, and drying. The dried, partially purified CCI-779 is then dissolved in acetone, clarified, and acetone removed. Following this, ether is added to crystallize product, heptanes added to the ether slurry, the slurry is filtered and dried. The resulting yield is 73% of CCI-779, having a strength of 93.5%, total impurities of less than 4% (i.e., 3.59%), and significantly, PhB(OH)2 of 0.007.

Workup

  1. customCrude CCI-779 was prepared essentially

Sources & evidence

ORD record
ord-4f059e7ed6f74825a78436afc8eed242
Source dataset
uspto-grants-2009_11
Patent number
US07622578B2

Linked notes

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