Calcium Chloride → HCID 67243068, compound

HRID 2422375Notes

Reaction equation

HRID 2422375 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@@H:19]([CH2:27][C:28]3[CH:29]=[N:30][C:31]([C:34]4[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][C:35]=4[CH2:42][CH3:43])=[CH:32][CH:33]=3)[C:20]([O:22]C(C)(C)C)=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Cl-:44].[Ca+2].[Cl-]>C(O)(C(F)(F)F)=O>[ClH:44].[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@@H:19]([CH2:27][C:28]3[CH:29]=[N:30][C:31]([C:34]4[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][C:35]=4[CH2:42][CH3:43])=[CH:32][CH:33]=3)[C:20]([OH:22])=[O:21])=[O:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 5284359Calcium ChlorideHCID 59157621HCID 59157621, compound

Product 1

HCID 67243068HCID 67243068, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 401 mg (0.69 mmol) of (2S)-tert-butyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(6-(2-ethyl-4-methoxyphenyl)pyridine-3-yl)propanoate in TFA (2.0 mL), protected from the atmosphere by a calcium chloride-filled drying tube was stirred at room temperature for two hours. The reaction mixture was concentrated in vacuo at less than 30° C. and the resulting orange oil was dissolved in ether to which a solution of 2 mL of 1 M HCl/ether was added. The resulting white solid was filtered and washed with ether to give the desired product as a white powder, 336 mg, 84% yield.

Workup

  1. additionfilled
  2. customdrying tube
  3. concentrationThe reaction mixture was concentrated in vacuo at less than 30° C.
  4. dissolutionthe resulting orange oil was dissolved in ether to which a solution of 2 mL of 1 M HCl/ether
  5. additionwas added
  6. filtrationThe resulting white solid was filtered
  7. washwashed with ether

Sources & evidence

ORD record
ord-da4ddd569694418ea82d4dac5997be75
Source dataset
uspto-grants-2011_06
Patent number
US07960349B2

Reaction notes

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