Calcium Chloride → HCID 86609630, compound

HRID 2422372Notes

Reaction equation

HRID 2422372 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]([Br:34])=[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-:35].[Ca+2].[Cl-]>C(O)(C(F)(F)F)=O>[ClH:35].[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([NH:18][CH:19]([CH2:27][C:28]3[CH:29]=[N:30][C:31]([Br:34])=[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 86609631HCID 86609631, compound

Product 1

HCID 86609630HCID 86609630, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1.02 g (1.95 mmol) of (2S)-tert-butyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(6-bromopyridin-3-yl)propanoate in TFA (3.0 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 35° C. and the resulting orange oil was dissolved in 3 mL of dichloromethane to which a solution of 6 mL of 1 M HCl/ether was added. The resulting white solid was filtered and washed with ether to give the title compound as a white powder, 845 mg, 86% yield.

Workup

  1. additionfilled
  2. customdrying tube
  3. concentrationThe reaction mixture was concentrated in vacuo at less than 35° C.
  4. dissolutionthe resulting orange oil was dissolved in 3 mL of dichloromethane to which a solution of 6 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-85022ed529184c95b81c9b5999a135ed
Source dataset
uspto-grants-2011_06
Patent number
US07960349B2

Reaction notes

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