Benzylamine → HCID 56953824, compound

HRID 871109Notes

Reaction equation

HRID 871109 reaction equation
[C:1]([NH:4]/[C:5](=[CH:9]\[O:10][CH3:11])/[C:6]([OH:8])=O)(=[O:3])[CH3:2].CN1CCOCC1.C(OC(Cl)=O)C(C)C.[CH2:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(Cl)Cl.O1CCCC1>[C:1]([NH:4]/[C:5](=[CH:9]\[O:10][CH3:11])/[C:6]([NH:34][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:8])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 86691065HCID 86691065, compound

Product 1

HCID 56953824HCID 56953824, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (D1) (20 g, 0.125 mol) in CH2Cl2 (300 ml, 15 vol) and tetrahydrofuran (THF) (100 ml, 5 vol), N-methylmorpholine (NMM) (16.6 ml, 0.15 mol) was added slowly at −40° C. After 20 min, isobutylchloroformate (IBCF) (19.67 ml, 0.15 mol) was added at same temperature and stirred for 20 min. Benzylamine (16.5 ml, 0.15 mol) in tetrahydrofuran (40 ml) was added at −40° C., then the reaction mixture was stirred for 1 h and allowed to room temperature. Solvent was evaporated under reduced pressure. The obtained crude was purified by column chromatography in 5% methanol in chloroform to afford (A1) as a white colored powder. Yield: 17 g; 55%.

Workup

  1. stirringthe reaction mixture was stirred for 1 h
  2. customallowed to room temperature
  3. customSolvent was evaporated under reduced pressure
  4. customThe obtained crude
  5. customwas purified by column chromatography in 5% methanol in chloroform

Sources & evidence

ORD record
ord-972720d7d0b546e2acf6ef226f9ecda0
Source dataset
uspto-grants-2015_03
Patent number
US08969620B2

Reaction notes

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