Dimethylamine → HCID 28165234, compound

HRID 2172686Notes

Reaction equation

HRID 2172686 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH3:13])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1CC[CH:17]([N:20]=[C:21]=NC2CCCCC2)CC1.CNC>C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]([C:10](=[O:11])[N:20]([CH3:21])[CH3:17])[CH3:13])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 10868DicyclohexylcarbodiimideHCID 637606BOC-D-alanine

Product 1

HCID 28165234HCID 28165234, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-2-tert-Butoxycarbonylamino-propionic acid (1.78 g, 9.43 mmol) in DCM (7.85 mL) was added portion wise DCC (2.14 g, 10.37 mmol) cooled in an ice bath. After stirring at room temperature for 30 min, dimethylamine (2 M in THF) (6.13 mL, 12.25 mmol) was added. The resulting solution was stirred overnight (18 h) until reaction was completed. The reaction mixture was filtered through silica gel and eluted with Ethyl acetate. Then the filtrate was evaporated off. The solvent was removed to yield (1.71 g, 7.12 mmol, 76% yield, 90% purity) ((R)-1-Dimethylcarbamoyl-ethyl)-carbamic acid tert-butyl ester as a yellow oil. The product was used in the next step without further purification.

Workup

  1. temperaturecooled in an ice bath
  2. stirringThe resulting solution was stirred overnight (18 h)
  3. customuntil reaction
  4. filtrationThe reaction mixture was filtered through silica gel
  5. washeluted with Ethyl acetate
  6. customThen the filtrate was evaporated off
  7. customThe solvent was removed

Sources & evidence

ORD record
ord-11e319770c644f299b9baba76b30b38f
Source dataset
uspto-grants-2015_06
Patent number
US09056843B2

Reaction notes

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