Ethyl diazoacetate → HCID 66744808, compound

HRID 1959481Notes

Reaction equation

HRID 1959481 reaction equation
[C:1]([O:5][C:6]([N:8]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C:9]1[C:10]([C:17]2[O:21][C:20]([C:22]3[CH:27]=[CH:26][C:25]([CH2:28][N:29]([CH3:37])[C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:24][CH:23]=3)=[N:19][N:18]=2)=[N:11][C:12]([CH:15]=[CH2:16])=[CH:13][N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+](=[CH:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])=[N-]>C1(C)C=CC=CC=1>[C:41]([O:40][C:38]([N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[C:9]1[N:14]=[CH:13][C:12]([CH:15]2[CH2:16][CH:47]2[C:48]([O:50][CH2:51][CH3:52])=[O:49])=[N:11][C:10]=1[C:17]1[O:21][C:20]([C:22]2[CH:27]=[CH:26][C:25]([CH2:28][N:29]([C:30]([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:36])[CH3:37])=[CH:24][CH:23]=2)=[N:19][N:18]=1)=[O:39])([CH3:44])([CH3:42])[CH3:43]

Participants

4

Reactant 2

HCID 12192Ethyl diazoacetate2×HCID 66745411HCID 66745411, compound

Product 1

HCID 66744808HCID 66744808, compoundYield 94.96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of tert-butyl N-[[4-[5-[3-[bis(tert-butoxycarbonyl)amino]-6-vinyl-pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]-N-methyl-carbamate (850 mg, 1.4 mmol) in toluene (0.2 mL) at 110° C. was added a solution of ethyl 2-diazoacetate (637 mg, 587 μL, 5.6 mol) in toluene (0.7 mL) slowly over a period of 30 minutes. The reaction mixture showed incomplete conversion to product, when stirred at room temperature, so another 4 equivalents of ethyl 2-diazoacetate (637 mg, 587 μL, 5.6 mmol) was added and the reaction mixture was heated at 110° C. for 20 minutes. The reaction mixture was cooled to room temperature and the solvent was evaporated under reduced pressure. The residue obtained was purified via silica gel column chromatography using 5 to 100% EtOAc in hexanes to yield ethyl 2-[5-[bis(tert-butoxycarbonyl)amino]-6-[5-[4-[[tert-butoxycarbonyl(methyl)amino]methyl]phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]cyclopropanecarboxylate (921 mg, 1.326 mmol, 94.96%). LC/MS m/z 595.6 [M+H-Boc]+.

Workup

  1. temperaturethe reaction mixture was heated at 110° C. for 20 minutes
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue obtained
  5. customwas purified via silica gel column chromatography

Sources & evidence

ORD record
ord-b838cb0382bb4b1d927185479e1f3423
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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