Trifluoroacetic acid → HCID 45279959, compound

HRID 218013

Reaction equation

HRID 218013 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]([OH:11])=O)=[N:7][CH:8]=1)#[N:2].C(N(C(C)C)CC)(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[NH2:54][C:55]1[CH:56]=[C:57]([C@@:66]23[N:75]=[C:74]([NH:76]C(=O)OC(C)(C)C)[S:73][CH2:72][C@@H:71]2[CH2:70][CH2:69][O:68][CH2:67]3)[C:58]2[O:62][C:61]([F:64])([F:63])[O:60][C:59]=2[CH:65]=1.C(O)(C(F)(F)F)=O.C(=O)(O)[O-].[Na+]>ClCCl.O>[NH2:76][C:74]1[S:73][CH2:72][C@H:71]2[C@:66]([C:57]3[C:58]4[O:62][C:61]([F:64])([F:63])[O:60][C:59]=4[CH:65]=[C:55]([NH:54][C:9]([C:6]4[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][N:7]=4)=[O:11])[CH:56]=3)([CH2:67][O:68][CH2:69][CH2:70]2)[N:75]=1

Participants

9

Reactant 6

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2724699PyBOPHCID 124007345-Cyanopyridine-2-carboxylic acidHCID 59281180tert-butyl (+/-)-[(4aR*,8aS*)-8a-(6-amino-2,2-difluorobenzo[1,3]dioxol-4-yl)-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-yl]carbamate

Product 1

HCID 45279959HCID 45279959, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

5-Cyanopyridine-2-carboxylic acid (4.0 mg), diisopropylethylamine (11.5 μl) and PyBOP (17.6 mg) were added to a solution of tert-butyl (±)-[(4aR*,8aS*)-8a-(6-amino-2,2-difluorobenzo[1,3]dioxol-4-yl)-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-yl]carbamate (10 mg) in dichloromethane (2.0 ml) in an ice bath. The mixture was heated to room temperature and stirred for four hours. The solvent was evaporated under reduced pressure and the residue was purified by NH-pTLC to obtain an intermediate. The resulting intermediate was dissolved in dichloromethane (3.0 ml) and TFA (1.0 ml) was added. After stirring at room temperature for four hours, the reaction solution was diluted with water and neutralized with a sodium bicarbonate solution. The aqueous layer was extracted with dichloromethane, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by NH-pTLC to obtain the title compound.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by NH-pTLC
  3. customto obtain an intermediate
  4. stirringAfter stirring at room temperature for four hours
  5. extractionThe aqueous layer was extracted with dichloromethane
  6. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by NH-pTLC

Sources & evidence

ORD record
ord-39bc75924af84a62a8b718f43cc4731a
Source dataset
uspto-grants-2012_06
Patent number
US08198269B2

Linked notes

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