Water → HCID 57466817, compound

HRID 601624

Reaction equation

HRID 601624 reaction equation
[OH:1][NH:2][C:3](=[NH:7])[CH2:4][CH2:5][CH3:6].[H-].[Na+].C(O[C:13](=O)[CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])C.O>CN(C=O)C>[C:20]([O:19][C:17](=[O:18])[NH:16][CH2:15][CH2:14][C:13]1[O:1][N:2]=[C:3]([CH2:4][CH2:5][CH3:6])[N:7]=1)([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 15933116Ethyl 3-{[(tert-butoxy)carbonyl]amino}propanoateHCID 178449909HCID 178449909, compound

Product 1

HCID 57466817HCID 57466817, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

N-Hydroxy-butyramidine (0.425 g, 4.16 mmol) in DMF (2 ml) is added to a stirred suspension of sodium hydride (0.183 g of a 60% dispersion in oil, 4.58 mmol) in the presence of molecular sieves (0.4 g). The reaction flask is then immersed in a pre-heated oil bath at 50° C. and stirring continued for 5 min. 3-tert-Butoxycarbonylamino-propionic acid ethyl ester (0.904 g, 4.16 mmol) in DMF (2 ml) is added over 5 min followed by more DMF (2 ml). After 3 h at 50° C. the mixture is cooled to 0° C. and water (3 ml) is added. The mixture is allowed to warm to room temperature then filtered through Celite™ filter material, washing with ethyl acetate, and the solvent is removed. Purification by chromatography, eluting with DCM:MeOH (95:5 increasing to 85:15) affords the titled compound.

Workup

  1. customThe reaction flask is then immersed in a pre-heated oil bath at 50° C.
  2. temperatureto warm to room temperature
  3. filtrationthen filtered through Celite™
  4. filtrationfilter material
  5. washwashing with ethyl acetate
  6. customthe solvent is removed
  7. customPurification by chromatography
  8. washeluting with DCM:MeOH (95:5 increasing to 85:15)

Sources & evidence

ORD record
ord-7c4b4ec3643944bea55102e646b2ee01
Source dataset
uspto-grants-2011_03
Patent number
US07902375B2

Linked notes

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