Diisopropylethylamine → HCID 131721948, compound

HRID 1871973Notes

Reaction equation

HRID 1871973 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH:13]=[C:12]([CH:14]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[CH:18]=[CH:17][C:16]4[CH:25]=[CH:26][CH:27]=[CH:28][C:15]3=4)[C:11](=[O:29])[NH:10][C:9]2=[O:30])[CH:5]=[CH:4][N:3]=1.Cl.[CH3:32][O:33][C:34](=[O:37])[CH2:35][NH2:36].C(N(CC)C(C)C)(C)C>CN1CCCC1=O>[CH:25]1[C:16]2[CH:17]=[CH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH:14]([C:12]3[C:11](=[O:29])[NH:10][C:9](=[O:30])[N:8]([C:6]4[CH:5]=[CH:4][N:3]=[C:2]([NH:36][CH2:35][C:34]([O:33][CH3:32])=[O:37])[N:7]=4)[CH:13]=3)[C:15]=2[CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 18689687HCID 18689687, compound

Product 1

HCID 131721948HCID 131721948, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of the product from example 6 step (i) (1 g), glycine methyl ester hydrochloride (0.339 g) and N,N-diisopropylethylamine (1.13 ml) in 1-methyl-2-pyrrolidinone (20 ml) was heated at 90° C. for 7 hours. The mixture was partitioned between ethyl acetate and water. The organic phase was washed with water, dried (MgSO4) and evaporated. The residue was dissolved in methanol/chloroform and the product precipitated by the addition of 50% ethyl acetate in isohexane. Yield 0.96 g.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washThe organic phase was washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. dissolutionThe residue was dissolved in methanol/chloroform
  6. customthe product precipitated by the addition of 50% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-a4cb30e58931426382804eeeb7aa29b3
Source dataset
uspto-grants-2000_08
Patent number
US06107297

Reaction notes

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