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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Trifluoroacetic acid → HCID 89726033, 화합물

HRID 592067
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HRID 592067 반응식
[N:1]1(C(OC(C)(C)C)=O)[CH2:6][CH2:5][N:4]([C:7]([O:9]C(C)(C)C)=O)[CH2:3][CH:2]1[C:14]([O:16]C)=[O:15].C(O)(C(F)(F)F)=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.[CH:63]([C:65]1[CH:66]=[C:67]([CH:71]=[CH:72][CH:73]=1)C(O)=O)=[O:64].[OH-].[Na+]>C(Cl)Cl.CN(C1C=CN=CC=1)C.CO>[CH:63]([C:65]1[CH:73]=[C:72]([CH:71]=[CH:67][CH:66]=1)[C:7]([N:4]1[CH2:5][CH2:6][NH:1][CH:2]([C:14]([OH:16])=[O:15])[CH2:3]1)=[O:9])=[O:64]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

10

반응물 6

HCID 6422Trifluoroacetic acidHCID 79724-MethylmorpholineHCID 120773-CarboxybenzaldehydeHCID 14798Sodium HydroxideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 224585731,4-Di-tert-butyl 2-methyl piperazine-1,2,4-tricarboxylate

생성물 1

HCID 89726033HCID 89726033, 화합물수율 100.7%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 887Methanol용매HCID 6344Dichloromethane용매3회

실험 절차

To a solution of 1,4-di-tert-butyl 2-methyl piperazine-1,2,4-tricarboxylate 29 (1.0 g, 2.9 mmol) in DCM (20 mL) was added TFA (2.31 g, 20.3 mmol) at 0° C. The reaction mixture was stirred at RT for 4 h. TLC analysis indicated complete conversion of SM. Reaction was concentrated to remove excess of TFA and sticky solid so obtained was taken in DCM (20 mL). To this suspension, HATU (1.65 g, 4.34 mmol), NMM (293 mg, 2.9 mmol), 3-formylbenzoic acid (435 mg, 2.9 mmol), and DMAP (10 mg) were added. Reaction mixture was stirred at RT for 16 h. The reaction was monitored by LCMS. The reaction mixture was diluted with DCM and washed with water; organic layer was separated, dried over Na2SO4 and concentrated under reduced pressure. The sticky solid so obtained was added to a solution of NaOH (65 mg, 1.6 mmol) in MeOH (5 mL). Reaction mixture was stirred at rt for 7 h. The reaction was monitored by TLC. When SM was completely consumed, reaction mixture was concentrated under vacuum. The solid was suspended in water and acidified to pH 6 using 1 N HCl. The suspension was filtered and the precipitate was triturated with ethanol to give 766 mg (20%) of 4-(3-formylbenzoyl)piperazine-2-carboxylic acid 32 as sticky solid.

후처리

  1. customReaction
  2. concentrationwas concentrated
  3. customto remove excess of TFA and sticky solid
  4. customso obtained
  5. customReaction mixture
  6. stirringwas stirred at RT for 16 h
  7. washwashed with water
  8. customorganic layer was separated
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated under reduced pressure
  11. customThe sticky solid so obtained
  12. customReaction mixture
  13. stirringwas stirred at rt for 7 h
  14. customWhen SM was completely consumed
  15. customreaction mixture
  16. concentrationwas concentrated under vacuum
  17. filtrationThe suspension was filtered
  18. customthe precipitate was triturated with ethanol

출처 및 근거

ORD 기록
ord-e35ea073a762484baee916053c96c33f
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09238656B2

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