9-Fluorenylmethyl chloroformate → HCID 71073375, compound

HRID 2408938Notes

Reaction equation

HRID 2408938 reaction equation
[C:1]([O:5][C:6](=[O:33])[NH:7][CH:8]([C:16](=[O:32])[NH:17][C:18]1([CH:22]([OH:31])[C:23](=[O:30])[NH:24][C:25]2[CH:29]=[CH:28][NH:27][N:26]=2)[CH2:21][CH2:20][CH2:19]1)[CH2:9][C:10]1([F:15])[CH2:14][CH2:13][CH2:12][CH2:11]1)([CH3:4])([CH3:3])[CH3:2].C([O-])(O)=O.[Na+].[C:39](Cl)([O:41][CH2:42][CH:43]1[C:55]2[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=2)[C:49]2[C:44]1=[CH:45][CH:46]=[CH:47][CH:48]=2)=[O:40]>O1CCOCC1.O.C(Cl)Cl>[CH:54]1[C:55]2[CH:43]([CH2:42][O:41][C:39]([N:27]3[CH:28]=[CH:29][C:25]([NH:24][C:23](=[O:30])[CH:22]([C:18]4([NH:17][C:16](=[O:32])[CH:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:33])[CH2:9][C:10]5([F:15])[CH2:14][CH2:13][CH2:12][CH2:11]5)[CH2:21][CH2:20][CH2:19]4)[OH:31])=[N:26]3)=[O:40])[C:44]3[C:49](=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:50]=2[CH:51]=[CH:52][CH:53]=1

Participants

6

Reactant 3

HCID 343679-Fluorenylmethyl chloroformateHCID 516892Sodium BicarbonateHCID 178453343HCID 178453343, compound

Product 1

HCID 71073375HCID 71073375, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

Compound 57-c (22.5 mg, 0.0482 mmol) was dissolved in a mixture of dioxane:water 1:1 (4 mL). NaHCO3 (14.2 mg, 0.168 mmol) was added to the solution followed by addition of Fmoc-Cl (48 mg, 0.18 mmol). The reaction mixture was stirred at room temperature for 16 h, diluted with DCM and extracted. The organic phase was washed with brine, dried over anh. Na2SO4 and concentrated. Purification by flash column chromatography (EtOAc/iso-Hexane, 0:100-40:60) gave the title compound (28 mg, 84%). MS m/z 690.3 (M+H)+.

Workup

  1. extractionextracted
  2. washThe organic phase was washed with brine
  3. dry with materialdried over anh. Na2SO4
  4. concentrationconcentrated
  5. customPurification by flash column chromatography (EtOAc/iso-Hexane, 0:100-40:60)

Sources & evidence

ORD record
ord-527f657105b94884be82b0295f92f18d
Source dataset
uspto-grants-2014_08
Patent number
US08815809B2

Reaction notes

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