Dichloromethane → HCID 75277251, compound

HRID 1429139Notes

Reaction equation

HRID 1429139 reaction equation
COC1C=CC(C[N:8]2[C:26](=[O:27])[N:25]3[CH:21]([CH2:22][CH:23]([O:28][C:29]4[CH:34]=[C:33]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)[N:32]=[C:31]([O:41][CH3:42])[N:30]=4)[CH2:24]3)[C:20](=[O:43])[NH:19][C:18]3([C:44]([NH:46][S:47]([C:50]4([CH3:53])[CH2:52][CH2:51]4)(=[O:49])=[O:48])=[O:45])[CH:16]([CH2:17]3)[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=CC=1.C(Cl)Cl.C([O-])(O)=O.[Na+]>C(O)(C(F)(F)F)=O>[CH3:42][O:41][C:31]1[N:30]=[C:29]([O:28][CH:23]2[CH2:22][CH:21]3[N:25]([C:26](=[O:27])[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]=[CH:15][CH:16]4[C:18]([C:44]([NH:46][S:47]([C:50]5([CH3:53])[CH2:52][CH2:51]5)(=[O:48])=[O:49])=[O:45])([NH:19][C:20]3=[O:43])[CH2:17]4)[CH2:24]2)[CH:34]=[C:33]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[N:32]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 72253702HCID 72253702, compound

Product 1

HCID 75277251HCID 75277251, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Compound 4a was dissolved in a 1:2 mixture of TFA:DCM (12 ml) and stirred at RT for 1 h. NaHCO3 was added and the organic layer was dried, filtered and evaporated. The afforded residue was purified by preparative HPLC which gave the pure title compound (36 mg, 16% over two steps), MS (M+H)+639.

Workup

  1. customthe organic layer was dried
  2. filtrationfiltered
  3. customevaporated
  4. customThe afforded residue was purified by preparative HPLC which

Sources & evidence

ORD record
ord-0de268cc01594eafabdb038723b7b498
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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