Tetrahydrofuran → HCID 135855915, compound

HRID 985115Notes

Reaction equation

HRID 985115 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][O:7][CH:8]=1)([OH:3])=O.C(Cl)CCl.[CH:13]1[CH:14]=[CH:15][C:16]2N(O)N=N[C:17]=2[CH:18]=1.CCN([CH:29]([CH3:31])[CH3:30])C(C)C.C[O:33]CN.[CH2:36]1C[O:39][CH2:38][CH2:37]1>CCOC(C)=O>[OH:33][C:17]1[CH:16]=[CH:15][C:14]([C:5]2[C:4]([CH:1]=[O:3])=[C:8]([C:30]3[CH:29]=[CH:31][C:38]([OH:39])=[CH:37][CH:36]=3)[O:7][N:6]=2)=[CH:13][CH:18]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 30144881,2-Oxazole-4-carboxylic acidHCID 177781771-MethoxymethanamineHCID 86583922HCID 86583922, compound

Product 1

HCID 135855915HCID 135855915, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Weinreb amide formation. 4-carboxy isoxazole (obtained from Steps 1-4 above) was dissolved in THF and activated with EDC:HOBt:DIEA (1.5:1.5:1.5) and allowed to stand at rt for 5min. N-methoxymethylamine (1.5 equiv.) was then added. The reaction mixture was allowed to stand at rt overnight, after which it was diluted with EtOAc and washed with 10% citric acid, 10% NaHCO3, and brine. The solvent was removed, and the residue was purified by flash chromatography (EtOAc/petrol) and lyophilized in 90% MeCN/H2O to give the desired product as a white powder.

Workup

  1. waitto stand at rt overnight
  2. washwashed with 10% citric acid, 10% NaHCO3, and brine
  3. customThe solvent was removed
  4. customthe residue was purified by flash chromatography (EtOAc/petrol)

Sources & evidence

ORD record
ord-fc228c0607964c1586ae2b1f93d0a863
Source dataset
uspto-grants-2005_03
Patent number
US06869969B2

Reaction notes

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