Sodium Bicarbonate → HCID 71090374, compound

HRID 716818Notes

Reaction equation

HRID 716818 reaction equation
[CH3:1][C:2]1([CH3:32])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][C:12]3[N:17]=[CH:16][C:15]([NH:18][C:19]([C@H:21]([NH:24]C(=O)OC(C)(C)C)[CH2:22][CH3:23])=[O:20])=[CH:14][CH:13]=3)[CH:9]=2)[CH2:4][O:3]1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:24][C@H:21]([CH2:22][CH3:23])[C:19]([NH:18][C:15]1[CH:16]=[N:17][C:12]([O:11][C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[CH2:4][O:3][C:2]3([CH3:1])[CH3:32])=[CH:13][CH:14]=1)=[O:20]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 71090133HCID 71090133, compound2×

Product 1

HCID 71090374HCID 71090374, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl N-[(1R)-1-[[6-[(3,3-dimethyl-1H-isobenzofuran-5-yl)oxy]-3-pyridyl]carbamoyl]propyl]carbamate (Intermediate 53, 25 mg, 0.0566 mmol) in DCM (2 mL) 2,2,2-trifluoroacetic acid (0.5 ml, 6.53 mmol) was added and the reaction mixture was stirred for 3 hours at 0° C. The reaction was diluted with DCM (10 ml) and an aqueous saturated solution of NaHCO3 was added while the pH was allowed to reach ˜8. Two phases were separated and the organic layer was dried (Na2SO4), filtered and evaporated to afford the title compound (18 mg) as white solid.

Workup

  1. customTwo phases were separated
  2. dry with materialthe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-0354a5f8342e4e98ad95b000f0b9058d
Source dataset
uspto-grants-2015_11
Patent number
US09193704B2

Reaction notes

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