Methanol → HCID 10703983, compound

HRID 623771Notes

Reaction equation

HRID 623771 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:14])[CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[CH3:17]CN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6]([N:8]([CH3:14])[CH2:9][CH2:10][C:11]([O:13][CH3:17])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27609523-(Methylamino)propanoic acid, N-BOC protected

Product 1

HCID 10703983HCID 10703983, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of 3-(tert-butoxycarbonyl(methyl)amino)propanoic acid (1.095 g, max. 5.29 mmol) in extra dry MeOH (0.24 mL, 5.93 mmol) and DCM (5 mL) was added DMAP (0.066 g, 0.539 mmol). EDCI (1.239 g, 6.47 mmol) was added and the reaction mixture allowed to warm up to room temperature. The reaction mixture was washed with aqueous 0.5 N HCl (3×10 mL), and brine (25 mL). The organic phase was dried over Na2SO4, filtered, and evaporated in vacuo to afford the desired product (1.129 g, 98% over two steps) as a colourless oil.

Workup

  1. washThe reaction mixture was washed with aqueous 0.5 N HCl (3×10 mL), and brine (25 mL)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-58d8cdb4e88f4794abd295c3d20cfdcf
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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