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Ammonium Chloride → HCID 59548966, compound

HRID 1895661
Notes
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Reaction equation

HRID 1895661 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:29][C:30]1[CH:35]=[C:34]([F:36])[C:33]([F:37])=[CH:32][C:31]=1[F:38])[CH2:10][C:11]([N:13]1[CH2:18][CH2:17][N:16]2[C:19]([C:25]([F:28])([F:27])[F:26])=[N:20][C:21]([C:22]([OH:24])=[O:23])=[C:15]2[CH2:14]1)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.[CH3:54][C:55]([CH3:58])([O-])[CH3:56].[K+].[Cl-].[NH4+]>C(O)(C)(C)C.C(N(CC)CC)C.ClCCl>[C:55]([O:23][C:22]([C:21]1[N:20]=[C:19]([C:25]([F:27])([F:28])[F:26])[N:16]2[CH2:17][CH2:18][N:13]([C:11](=[O:12])[CH2:10][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:29][C:30]3[CH:35]=[C:34]([F:36])[C:33]([F:37])=[CH:32][C:31]=3[F:38])[CH2:14][C:15]=12)=[O:24])([CH3:58])([CH3:56])[CH3:54]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 23665647Potassium tert-butoxideHCID 59548952(R)-7-[3-tert-butoxycarbonylamino-4-(2,4,5-trifluoro-phenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid

Product 1

HCID 59548966HCID 59548966, compound
Yield 33.6%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolvent2×HCID 8471TriethylamineSolvent

Procedure

(R)-7-[3-tert-Butoxycarbonylamino-4-(2,4,5-trifluoro-phenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid 2a (0.3 g, 0.54 mmol), 10 mL of dichloromethane and 5 mL of tert-butanol were added into a 100 mL reaction flask, followed by addition of 0.3 mL of triethylamine and bis(2-oxo-3-oxazolidinyl)phosphinic chloride (0.277 g, 1.09 mmol) under stirring. After stirring at room temperature for 2 hours, 10 mL of tert-butanol and potassium tert-butoxide (0.24 g, 2.16 mmol) were added to the solution. The reaction mixture was stirred at room temperature for another 2 hours and monitored by thin layer chromatography until the disappearance of the starting materials. 10 mL of saturated ammonium chloride was added to the reaction mixture and white precipitates were formed. The precipitates were filtered through a pad of 100-200 mesh silica gel and 50 mL of water was added to the filtrate. Then the filtrate was extracted with ethyl acetate (25 mL×5). The combined organic phase was washed with 30 mL of saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (R)-7-[3-tert-butoxycarbonylamino-4-(2,4,5-trifluoro-phenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid tert-butyl ester 36a (0.11 g, yield 33.6%) as a white solid.

Workup

  1. stirringAfter stirring at room temperature for 2 hours
  2. stirringThe reaction mixture was stirred at room temperature for another 2 hours
  3. customwhite precipitates
  4. customwere formed
  5. filtrationThe precipitates were filtered through a pad of 100-200 mesh silica gel and 50 mL of water
  6. additionwas added to the filtrate
  7. extractionThen the filtrate was extracted with ethyl acetate (25 mL×5)
  8. washThe combined organic phase was washed with 30 mL of saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4a92af5b88404fadbde3e14589bdc347
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08513411B2

Reaction notes

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