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Chloride → HCID 21201649, compound

HRID 1979380
Notes
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Reaction equation

HRID 1979380 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl[C:14](Cl)([O:16]C(=O)OC(Cl)(Cl)Cl)Cl.[C:25]([C:29]([CH2:31][N:32]1[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=2[N:36]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=2[F:49])[CH2:35][CH:34]([NH2:50])[C:33]1=[O:51])=[O:30])([CH3:28])([CH3:27])[CH3:26].[Cl-]>O1CCCC1.C(N(CC)CC)C>[C:25]([C:29]([CH2:31][N:32]1[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=2[N:36]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=2[F:49])[CH2:35][CH:34]([NH:50][C:14]([NH:1][C:2]2[CH:12]=[CH:11][CH:10]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:3]=2)=[O:16])[C:33]1=[O:51])=[O:30])([CH3:28])([CH3:26])[CH3:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 312ChlorideHCID 11400Ethyl 3-aminobenzoateHCID 94429TriphosgeneHCID 21201731HCID 21201731, compound

Product 1

HCID 21201649HCID 21201649, compoundYield 223.5%

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
2×
HCID 8471TriethylamineSolvent

Procedure

Ethyl 3-aminobenzoate (69 mg) was dissolved in tetrahydrofuran (10 ml), the solution was cooled on ice-water. Triphosgene (45 mg) was added at internal temperature 5° C., triethylamine (162 mg) was added thereto over 10 minutes period, the mixture was allowed to come to room temperature and stirred for 10 minutes. A solution of 1-tert-butylcarbonylmethyl-2-oxo-3-amino-5-(2-fluorophenyl)-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (150 mg) in tetrahydrofuran (5 ml), the mixture was additionally chloride. The organic layer was successively washed with water and saturated brine, dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography(n-hexane:ethyl acetate=3:1), to thereby obtain 190 mg of the title compound as colorless crystals (Yield: 83%).

Workup

  1. temperaturethe solution was cooled on ice-water
  2. additionwas added
  3. customto come to room temperature
  4. washThe organic layer was successively washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography(n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-d58a158b89b14b26afd1e6ec05a8f33c
Source dataset
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06239131B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes