Trifluoromethanesulfonic acid → HCID 136387741, compound

HRID 1924381Notes

Reaction equation

HRID 1924381 reaction equation
[CH:1]([C@@H:4]1[NH:28][C:27]2[O:29][C:24](=[N:25][N:26]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][C:18]2[CH:30]=[C:31]3[C:15](=[CH:16][CH:17]=2)[CH:14]=[CH:13][N:12]=[C:11]3[O:10][C@H:9]2[CH2:32][N:6]([C@H:7]([C:33]([O:35][CH3:36])=[O:34])[CH2:8]2)[C:5]1=[O:37])([CH3:3])[CH3:2].OS(C(F)(F)F)(=O)=O.[I:46]N1C(=O)CCC1=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[I:46][C:14]1[C:15]2[C:31]3=[CH:30][C:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]4[O:29][C:27]([NH:28][C@@H:4]([CH:1]([CH3:3])[CH3:2])[C:5](=[O:37])[N:6]5[CH2:32][C@H:9]([O:10][C:11]3=[N:12][CH:13]=1)[CH2:8][C@H:7]5[C:33]([O:35][CH3:36])=[O:34])=[N:26][N:25]=4)=[CH:17][CH:16]=2

Participants

6

Reactant 4

HCID 62406Trifluoromethanesulfonic acidHCID 120273N-Iodosuccinimide2×HCID 516892Sodium BicarbonateHCID 136387742HCID 136387742, compound

Product 1

HCID 136387741HCID 136387741, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0.3 M solution of methyl (3R,5S,8S)-8-isopropyl-7-oxo-2,28-dioxa-6,9,11,12,25-pentaazapentacyclo[17.6.2.13,6.110,13.022,26]noncosa-1(25),10,12,19,21,23,26-heptaene-5-carboxylate (from Step 1) in dry DCM was added triflic acid (2 eq) and N-iodosuccinimide (2 eq) and the mixture was stirred under N2 for 16 h. An additional portion of N-iodosuccinimide (2 eq) was added and the reaction was stirred for additional 24 h. The reaction mixture was poured into saturated NaHCO3 and extracted with DCM (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The resulting crude compound was purified on silica gel (20% to 40% EtOAc in PE) to yield the compound as a yellow solid. MS (ES+) C27H32IN5O5 requires: 633. Found: 634 (M+H+).

Workup

  1. stirringthe reaction was stirred for additional 24 h
  2. extractionextracted with DCM (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting crude compound was purified on silica gel (20% to 40% EtOAc in PE)

Sources & evidence

ORD record
ord-59e6ed0c5d8e49a3b7d9e930b8319b67
Source dataset
uspto-grants-2012_05
Patent number
US08178520B2

Reaction notes

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