Water → HCID 86663348, compound

HRID 386705Notes

Reaction equation

HRID 386705 reaction equation
[NH:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3][C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:21][C:22]([N:24]([CH2:28][CH2:29][CH3:30])[CH2:25][CH2:26][CH3:27])=[O:23].O>CN(C=O)C.C(Cl)Cl.CCCCCCC>[CH2:25]([N:24]([CH2:28][CH2:29][CH3:30])[C:22]([CH2:21][O:5][C:4](=[O:6])[CH2:3][CH2:2][NH:1][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[O:23])[CH2:26][CH3:27]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 2196472-chloro-N,N-dipropylacetamide

Product 1

HCID 86663348HCID 86663348, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolventHCID 8900HeptaneSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred suspension of Boc-Beta-Ala-OH (40.0 g, 211 mmol) in DMF (200 ml) at 60° C. under N2 was added potassium carbonate (40.0 g, 289 mmol). To this mixture was added 2-chloro-N,N-dipropyl-acetamide (36.7 g, 207 mmol) in DMF (75 ml). The reaction mixture was allowed to stir at 60° C. overnight. The reaction was allowed to cool to RT and diluted with DCM (400 ml) followed by water (500 ml). The organic layer was separated and washed with brine (200 ml), dried over MgSO4 and concentrated in vacuo to yield a pale yellow oil. To the oil was added n-heptane (500 ml) (azeotrope for DMF) which was concentrated in vacuo to afford the title compound; LC-MS Rt 1.14 mins; 331.3 [M+H]+, Method 2minLC_v003.

Workup

  1. temperatureto cool to RT
  2. customThe organic layer was separated
  3. washwashed with brine (200 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto yield a pale yellow oil
  7. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-18ed123d7ca34f95b15520962870d174
Source dataset
uspto-grants-2013_02
Patent number
US08372845B2

Reaction notes

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