Trifluoroacetic acid → HCID 178499928, compound

HRID 2370928Notes

Reaction equation

HRID 2370928 reaction equation
C([SiH](CC)CC)C.FC(F)(F)C(O)=O.[C:15]([O:19][C:20]([NH:22][C:23]1[N:28]=[CH:27][C:26]([CH2:29][C:30]([C:39]2[N:40]=[CH:41][N:42](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:43]=2)([C:35]([O:37][CH3:38])=[O:36])[C:31]([O:33][CH3:34])=[O:32])=[CH:25][CH:24]=1)=[O:21])([CH3:18])([CH3:17])[CH3:16].[OH-].[Na+]>C(Cl)Cl.O>[C:15]([O:19][C:20]([NH:22][C:23]1[N:28]=[CH:27][C:26]([CH2:29][C:30]([C:39]2[N:40]=[CH:41][NH:42][CH:43]=2)([C:35]([O:37][CH3:38])=[O:36])[C:31]([O:33][CH3:34])=[O:32])=[CH:25][CH:24]=1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 14798Sodium HydroxideHCID 69331493HCID 69331493, compound

Product 1

HCID 178499928HCID 178499928, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

0.20 g (1.70 mmol, 272 μl) of triethylsilane and 1.76 g (15.46 mmol, 1.19 ml) of trifluoroacetic acid were added to a solution of 1.00 g (1.55 mmol) of the compound from example 12c in 15 ml of CH2Cl2 while cooling in ice and stirring, and stirring was continued at 0° C. After 5 h, while cooling in ice, 10 ml of water were added and the pH was adjusted to 9 with 2N NaOH. The resulting precipitate was filtered off with suction, triturated in about 20 ml of CH2Cl2, filtered off with suction and dried. 0.55 g of the desired compound was obtained.

Workup

  1. temperaturewhile cooling in ice
  2. stirringstirring
  3. customwas continued at 0° C
  4. temperaturewhile cooling in ice
  5. filtrationThe resulting precipitate was filtered off with suction
  6. customtriturated in about 20 ml of CH2Cl2
  7. filtrationfiltered off with suction
  8. customdried

Sources & evidence

ORD record
ord-6f507a40ebad41fcb6cd06303f541868
Source dataset
uspto-grants-2014_04
Patent number
US08710232B2

Reaction notes

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