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Diisopropylethylamine → HCID 53349361, compound

HRID 2357097
Notes
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Reaction equation

HRID 2357097 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:25]([O:29][C:30]([N:32]1[C@@:36]([CH3:40])([C:37]([OH:39])=O)[CH2:35][O:34][C:33]1([CH3:42])[CH3:41])=[O:31])([CH3:28])([CH3:27])[CH3:26].C(N(CC)C(C)C)(C)C.[CH2:52]([O:60][C:61]1[CH:70]=[CH:69][C:64]([C:65]([NH:67][NH2:68])=[O:66])=[CH:63][C:62]=1[C:71]([F:74])([F:73])[F:72])[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59]>ClCCl.CN(C)C=O>[CH3:41][C:33]1([CH3:42])[N:32]([C:30]([O:29][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:31])[C@:36]([CH3:40])([C:37]([NH:68][NH:67][C:65](=[O:66])[C:64]2[CH:69]=[CH:70][C:61]([O:60][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])=[C:62]([C:71]([F:72])([F:74])[F:73])[CH:63]=2)=[O:39])[CH2:35][O:34]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 52987736HCID 52987736, compoundHCID 533493604-(Octyloxy)-3-(trifluoromethyl)benzohydrazide

Product 1

HCID 53349361HCID 53349361, compound
Yield 109.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20.5 °C

Procedure

A 5 L round bottom flask was inerted and charged with HATU (199 g, 0.52 mol, 1.2 equiv), N,N-dimethylformamide (380 mL), and mixed. A solution of (R)-3-(tert-butoxycarbonyl)-2,2,4-trimethyloxazolidine-4-carboxylic acid (D3A) (133.1 g, 0.43 mol, 1 equiv), dichloromethane (870 mL), and N,N-diisopropylethylamine (155 mL, 0.88 mol, 2 equiv) was charged to the flask over 15 minutes. The resulting mixture was stirred at 18 to 23° C. for 1 hour. A solution of benzohydrazide (D6) (145 g, 0.43 mol, 1 equiv) in dichloromethane (1120 mL), and N,N-Dimethylformamide (420 mL) was charged over 15 minutes then stirred at 18 to 23° C. for 1 hour. After 1 hour, TLC indicated the reaction was complete. The mixture was concentrated, partitioned between ethyl acetate (2.5 L) and water (2.5 L). The phases were split and the aqueous extracted once more with ethyl acetate (1 L). The organic phases were combined, washed with 10% w/v sodium chloride (2×1 L), dried with magnesium sulfate, filtered over Celite, and concentrated under vacuum to afford the crude product (367 g, 146% yield). The crude material was purified using a silica-gel column (2 kg) which was eluted with 5 to 25% ethyl acetate in heptane to give the title product (270 g, 108% yield, 95.9% AUC by HPLC) as a yellow oil.

Workup

  1. customA 5 L round bottom flask was inerted
  2. additionmixed
  3. stirringthen stirred at 18 to 23° C. for 1 hour
  4. waitAfter 1 hour
  5. concentrationThe mixture was concentrated
  6. custompartitioned between ethyl acetate (2.5 L) and water (2.5 L)
  7. customThe phases were split
  8. extractionthe aqueous extracted once more with ethyl acetate (1 L)
  9. washwashed with 10% w/v sodium chloride (2×1 L)
  10. dry with materialdried with magnesium sulfate
  11. filtrationfiltered over Celite
  12. concentrationconcentrated under vacuum
  13. customto afford the crude product (367 g, 146% yield)
  14. customThe crude material was purified
  15. washwas eluted with 5 to 25% ethyl acetate in heptane

Sources & evidence

ORD record
ord-9a1a86adc17744f4997fb1fb2c175b16
Source dataset
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07759370B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes