Tetrabutylammonium Fluoride → HCID 86612274, compound

HRID 1441975Notes

Reaction equation

HRID 1441975 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][C:36]([F:39])=[C:35]([CH2:40][C@H:41]([N:46]([C:48](=[O:72])[C@H:49]([NH:64][C:65]([O:67][C:68]([CH3:71])([CH3:70])[CH3:69])=[O:66])[CH2:50][CH2:51][CH2:52][NH:53][C:54]([O:56][CH2:57][C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)=[O:55])[CH3:47])[C:42]([O:44][CH3:45])=[O:43])[CH:34]=2)=[CH:29][C:28]=1[CH2:73][C@H:74]([NH:84][C:85]([O:87][CH2:88][C:89]1[CH:94]=[CH:93][CH:92]=[CH:91][CH:90]=1)=[O:86])[C:75]([O:77]CC[Si](C)(C)C)=[O:76])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1.CN(C=O)C>[CH2:19]([O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][C:36]([F:39])=[C:35]([CH2:40][C@H:41]([N:46]([C:48](=[O:72])[C@H:49]([NH:64][C:65]([O:67][C:68]([CH3:69])([CH3:71])[CH3:70])=[O:66])[CH2:50][CH2:51][CH2:52][NH:53][C:54]([O:56][CH2:57][C:58]3[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=3)=[O:55])[CH3:47])[C:42]([O:44][CH3:45])=[O:43])[CH:34]=2)=[CH:29][C:28]=1[CH2:73][C@H:74]([NH:84][C:85]([O:87][CH2:88][C:89]1[CH:90]=[CH:91][CH:92]=[CH:93][CH:94]=1)=[O:86])[C:75]([OH:77])=[O:76])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86761053HCID 86761053, compound

Product 1

HCID 86612274HCID 86612274, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1.9 ml of 1N tetrabutylammonium fluoride in THF are added dropwise to a solution of 980 mg (0.922 mmol) of 2-(trimethylsilyl)ethyl (2S)-3-(4-(benzyloxy)-3′-{(2S)-2-[{(2R)-5-{[(benzyloxy)carbonyl]amino}-2-[(tert-butoxycarbonyl)amino]pentanoyl}(methyl)amino]-3-methoxy-3-oxopropyl }-4′-fluorobiphenyl-3-yl)-2-{[(benzyloxy)carbonyl]amino}propanoate (Example 19O) in 20 ml of absolute DMF. After 60 min at RT, the mixture is cooled to 0° C., and ice-water is added. The mixture is immediately extracted with dichloromethane. The organic phase is dried over magnesium sulfate, concentrated in vacuo and dried under high vacuum. The crude product is reacted without further purification.

Workup

  1. extractionThe mixture is immediately extracted with dichloromethane
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customdried under high vacuum
  5. customThe crude product is reacted without further purification

Sources & evidence

ORD record
ord-cee7085888eb4f4da7d95c0d0743bbe5
Source dataset
uspto-grants-2010_02
Patent number
US07655643B2

Reaction notes

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