Diisopropylethylamine → HCID 77709006, compound

HRID 1883484Notes

Reaction equation

HRID 1883484 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C:11]([OH:13])=O)=[CH:5][CH:4]=1)#[N:2].[C:20]([O:24][C:25](=[O:35])[CH2:26][NH:27][CH2:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)([CH3:23])([CH3:22])[CH3:21].[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.C(N(C(C)C)CC)(C)C>CN(C)C=O>[C:20]([O:24][C:25](=[O:35])[CH2:26][N:27]([C:11](=[O:13])[CH:10]([CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[CH2:9][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=1)[CH2:28][CH:29]1[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]1)([CH3:23])([CH3:21])[CH3:22]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 11414215HCID 11414215, compoundHCID 17901841HCID 17901841, compound

Product 1

HCID 77709006HCID 77709006, compoundYield 110.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3-(4-cyano-phenyl)-2-(R,S)-cyclohexyl-propionic acid (5 g, 19.43 mmol) and (cyclohexylmethyl-amino)-acetic acid tert-butyl ester (4.42 g, 19.43 mmol) in dimethylformamide (50 ml) were added TOTU (7.01 g, 21.37 mmol) and diisopropylethyl amine (2.51 g, 19.43 mmol) at −15° C. The mixture was stirred for 1 hour and then allowed to warm to room temperature. After evaporation, the residue was treated with sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was evaporated to yield 10 g of crude material which was used in the next step without further purification, MS m/z: 467.4 (M+H)+.

Workup

  1. customAfter evaporation
  2. additionthe residue was treated with sodium bicarbonate solution
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-d3b55f44a1324895bedbcf35c4a2f8ee
Source dataset
uspto-grants-2004_07
Patent number
US06759420B1

Reaction notes

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