Diisopropylethylamine → HCID 69934617, compound

HRID 2416641Notes

Reaction equation

HRID 2416641 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[C:18]([O:22][C:23]([NH:25][C@@H:26]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1)[C:27]([OH:29])=O)=[O:24])([CH3:21])([CH3:20])[CH3:19].Cl.Cl.[NH2:39][CH2:40][C:41]([N:43]1[CH2:48][CH2:47][N:46]([C:49]2[CH:54]=[CH:53][C:52]([Cl:55])=[CH:51][CH:50]=2)[CH2:45][CH2:44]1)=[O:42].C(N(C(C)C)CC)(C)C>CN(C)C=O.C(=O)([O-])O.[Na+]>[C:18]([O:22][C:23]([NH:25][C@@H:26]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1)[C:27]([NH:39][CH2:40][C:41]([N:43]1[CH2:44][CH2:45][N:46]([C:49]2[CH:54]=[CH:53][C:52]([Cl:55])=[CH:51][CH:50]=2)[CH2:47][CH2:48]1)=[O:42])=[O:29])=[O:24])([CH3:19])([CH3:20])[CH3:21]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 2734482Boc-3-(2-pyridyl)-Ala-OHHCID 22633064HCID 22633064, compound

Product 1

HCID 69934617HCID 69934617, compoundYield 96.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Diphenylphosphoryl azide (25 g) was added to a solution of (2S)-2-(tert-butoxycarbonylamino)-3-(2-pyridyl)propanoic acid (23 g) in N,N-dimethylformamide (230 ml) at 5° C. To the mixture was added a solid of 2-amino-1-[4-(4-chlorophenyl)-1-piperazinyl]-ethan-1-one dihydrochloride (28.2 g) at 5° C. with stirring and then diisopropylethylamine (47 ml) was added dropwise at 7-10° C. The mixture was stirred at 7-10° C. for 30 minutes and at room temperature for 2 hours. The mixture was diluted with saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The aqueous layer was extracted with two 500-ml portions of ethyl acetate, and the combined organic layers were extracted with 1N hydrochloric acid (150 ml×2). The combined aqueous layers were basified (pH 9) with sodium hydrogencarbonate and extracted with ethyl acetate. The organic layer was washed thoroughly with aqueous sodium hydrogencarbonate solution and brine, dried over magnesium sulfate and concentrated in vacuo to give the title compound (42 g).

Workup

  1. stirringThe mixture was stirred at 7-10° C. for 30 minutes and at room temperature for 2 hours
  2. extractionextracted with ethyl acetate
  3. extractionThe aqueous layer was extracted with two 500-ml portions of ethyl acetate
  4. extractionthe combined organic layers were extracted with 1N hydrochloric acid (150 ml×2)
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed thoroughly with aqueous sodium hydrogencarbonate solution and brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c4f200baf2514fc5a386c77a17e916b4
Source dataset
uspto-grants-2004_11
Patent number
US06825200B1

Reaction notes

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