Bicarbonate Ion → HCID 68683616, compound

HRID 2234360Notes

Reaction equation

HRID 2234360 reaction equation
CC(OC([NH:8][CH:9]1[C@@H:14]2[C@H:10]1[CH2:11][N:12]([C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[CH2:13]2)=O)(C)C.C(O)(C(F)(F)F)=O.C(=O)(O)[O-].C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[NH2:8][CH:9]1[C@@H:14]2[C@H:10]1[CH2:11][N:12]([C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[CH2:13]2

Participants

6

Reactant 4

HCID 769Bicarbonate IonHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 11244469HCID 11244469, compound2×

Product 1

HCID 68683616HCID 68683616, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl(1R,5S)-6-[(2-methylpropan-2-yl)oxycarbonylamino]-3-azabicyclo[3.1.0]hexane-3-carboxylate (Bioorganic & Medicinal Chemistry Letters (2004), 14(11), 2773-2776, Compound 9; 6.74 g, 20.3 mmol) was stirred and dissolved in DCM (90 mL) at ambient temperature and TFA (10 ml) was added. The solution was stirred at room temperature for 2 hours. Sat. bicarbonate (100 ml) was added followed by potassium carbonate solid until neutral. The DCM layer was separated and washed once more with water. The DCM solution was dried (MgSO4), filtered and evaporated to a gum.

Workup

  1. customThe DCM layer was separated
  2. washwashed once more with water
  3. dry with materialThe DCM solution was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to a gum

Sources & evidence

ORD record
ord-32430aafd8a246e2b4e46423e76c0bf9
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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