HCID 136387708, compound → HCID 136387707, compound

HRID 1891245Notes

Reaction equation

HRID 1891245 reaction equation
[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][CH:6]([N:14]([CH2:21][C:22]1[N:23]=[C:24]2[C:29](=[N:30][CH:31]=1)[N:28]=[C:27]([NH:32][C:33](=[O:37])[CH:34]([CH3:36])[CH3:35])[NH:26][C:25]2=[O:38])[C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])[C:7]([O:9]C(C)(C)C)=[O:8]>C(O)(C(F)(F)F)=O.ClCCl>[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][CH:6]([N:14]([CH2:21][C:22]1[N:23]=[C:24]2[C:29](=[N:30][CH:31]=1)[N:28]=[C:27]([NH:32][C:33](=[O:37])[CH:34]([CH3:35])[CH3:36])[NH:26][C:25]2=[O:38])[C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])[C:7]([OH:9])=[O:8]

Participants

4

Reactant 1

HCID 136387708HCID 136387708, compound

Product 1

HCID 136387707HCID 136387707, compoundYield 120.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The ester 143 (2 g, 2.9 mmol) was dissolved in 20 mL of 50% TFA in dichloromethane and the solution was stirred at room temperature for 30 min. after which the TLC showed the complete disappearance of the starting ester. The reaction mixture was concentrated and the residue was crystallized from CH2Cl2:Hexanes (2:3) and crystallized product was filtered off and dried to obtain the pure product 144 (1.76 g, 96%) as off white powder. 1H NMR (DMSO-d6, 400 MHz) δ=12.32 (bs, 1H), 11.94 (s, 1H), 8.88 (s, 1H), 8.84 (d, J=7.4 Hz, 1H), 7.90 (d, J=8.3 Hz, 2H), 7.69 (d, J=8.3 Hz, 2H), 5.22 (s, 2H), 4.45-4.41 (m, 1H), 3.62 (s, 3H), 2.78-2.75 (m, 1H), 2.35 (t, J=7.4 Hz, 2H) 2.07-1.92 (m, 2H), 1.12 (d, J=6.8 Hz, 6H). 13C NMR DMSO-d6) δ=180.77, 173.70, 172.19, 165.70, 159.21, 155.54, 149.93, 149.84, 147.75, 141.78, 134.18, 130.53, 128.71, 128.49, 117.51, 114.64, 53.98, 52.06, 51.93, 34.97, 30.11, 25.68, 18.73. MS. Molecular weight calculated for C26H26F3N7O8, Cal. 621.18, Found 620.18 (M−H−).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was crystallized from CH2Cl2:Hexanes (2:3)
  3. customcrystallized product
  4. filtrationwas filtered off
  5. customdried

Sources & evidence

ORD record
ord-806223929e924867acb4a4caae8dbc78
Source dataset
uspto-grants-2013_08
Patent number
US08507455B2

Reaction notes

Loading…