Diisopropylethylamine → HCID 54347045, compound

HRID 1953921Notes

Reaction equation

HRID 1953921 reaction equation
[CH3:1][N:2]([CH3:20])[C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]([CH3:17])[C@@H:9]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:10]([OH:12])=O)=[CH:5][CH:4]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[NH2:54][CH:55]([CH2:68][C:69]1[CH:74]=[CH:73][C:72]([O:75][CH2:76][C:77]2[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=2)=[CH:71][CH:70]=1)[C:56]([NH:58][CH:59]1[CH2:64][CH2:63][CH2:62][N:61]([CH2:65][CH2:66][CH3:67])[CH2:60]1)=[O:57]>CN(C=O)C.C(OCC)(=O)C>[CH2:76]([O:75][C:72]1[CH:73]=[CH:74][C:69]([CH2:68][CH:55]([NH:54][C:10](=[O:12])[CH:9]([N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([N:2]([CH3:1])[CH3:20])=[CH:19][CH:18]=2)[CH3:17])[CH2:13][CH:14]([CH3:16])[CH3:15])[C:56](=[O:57])[NH:58][CH:59]2[CH2:64][CH2:63][CH2:62][N:61]([CH2:65][CH2:66][CH3:67])[CH2:60]2)=[CH:70][CH:71]=1)[C:77]1[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 23297590HCID 23297590, compoundHCID 54010435HCID 54010435, compound

Product 1

HCID 54347045HCID 54347045, compoundYield 51.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-2-[(4-dimethylamino-benzyl)-methyl-amino]-4-methyl-pentanoic acid (0.28 g, 1.01 mmol) in 15 mL of DMF was added HBTU (0.38 g, 1.01 mmol) and diisopropylethylamine (0.65 g, 5.05 mmol). The mixture was stirred for 30 minutes at 0° C. A solution of 2-amino-3-(4-benzyloxyphenyl)-N-(1-propyl-piperidin-3-yl)propionamide (0.40 g, 1.01 mmol) in 15 mL of DMF was added to the reaction mixture. The reaction mixture was allowed to reach the room temperature and was stirred for another 30 minutes. The mixture was diluted with 40 mL of ethyl acetate, washed with 1N HCl (2×10 mL), saturated NaHCO3 (2×10 mL) and saturated solution of brine (2×10 mL). The organic layer was separated, dried with Na2SO4 and evaporated to dryness. The crude residue was purified by chromatography (silica gel, 6:4 hexane/ethyl acetate). The purified product was crystallized from methylene chloride and petroleum ether to give the title compound (0.34 g, 49%) as a white powder; mp 131-133° C.

Workup

  1. customthe room temperature
  2. stirringwas stirred for another 30 minutes
  3. washwashed with 1N HCl (2×10 mL), saturated NaHCO3 (2×10 mL) and saturated solution of brine (2×10 mL)
  4. customThe organic layer was separated
  5. dry with materialdried with Na2SO4
  6. customevaporated to dryness
  7. customThe crude residue was purified by chromatography (silica gel, 6:4 hexane/ethyl acetate)
  8. customThe purified product was crystallized from methylene chloride and petroleum ether

Sources & evidence

ORD record
ord-5a675aa97ad44bd3a3a71044da17db08
Source dataset
uspto-grants-2000_09
Patent number
US06117841

Reaction notes

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