Dichloromethane → HCID 66895863, compound

HRID 337570Notes

Reaction equation

HRID 337570 reaction equation
CC([C:5]1([N:8]([CH2:12][C:13]2[CH:18]=[C:17]([CH2:19][CH2:20][NH2:21])[CH:16]=[C:15]([Cl:22])[C:14]=2[Cl:23])[C:9](=[O:11])[O-:10])[CH2:7][CH2:6]1)(C)C.CCN([CH:30]([CH3:32])[CH3:31])C(C)C.Cl[C:34]([O:36][CH3:37])=[O:35].Cl[CH2:39]Cl>CCOCC>[CH:5]1([N:8]([CH2:12][C:13]2[CH:18]=[C:17]([CH2:19][CH2:20][NH:21][C:34]([O:36][CH3:37])=[O:35])[CH:16]=[C:15]([Cl:22])[C:14]=2[Cl:23])[C:9](=[O:11])[O:10][C:30]([CH3:32])([CH3:39])[CH3:31])[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 86651665HCID 86651665, compound

Product 1

HCID 66895863HCID 66895863, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1,1-dimethylethyl{[5-(2-aminoethyl)-2,3-dichlorophenyl]methyl}cyclopropylcarbamate (1 eq.) from the previous step in dichloromethane (0.07 M) was added sequentially at 0 Hunig's base (1.2 eq.) and methyl chloroformate. The resulting solution was then allowed to warm slowly to RT over 3 h. The crude reaction mixture was subsequently diluted with ether and washed sequentially with 1 N aq. NaOH, 1 N aq. HCl, water and brine. The ether extract was then dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 19:1 (v/v) Hex:EtOAc→EtOAc) afforded the title compound as a pale yellow oil.

Workup

  1. customThe crude reaction mixture
  2. washwashed sequentially with 1 N aq. NaOH, 1 N aq. HCl, water and brine
  3. extractionThe ether extract
  4. dry with materialwas then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customPurification of the crude product
  8. customthus obtained by way of flash chromatography (SiO2, 19:1 (v/v) Hex:EtOAc→EtOAc)

Sources & evidence

ORD record
ord-5161c8b224cb45638348dcc303bee560
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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