Diisopropylethylamine → (S)-tert-butyl (1-((2-(2-(2-(diethoxyphosphoryl)ethoxy)ethoxy)ethyl)amino)-1-oxopropan-2-yl)carbamate

HRID 2407938Notes

Reaction equation

HRID 2407938 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH3:13])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:47][CH2:48][CH2:49][O:50][CH2:51][CH2:52][O:53][CH2:54][CH2:55][P:56](=[O:63])([O:60][CH2:61][CH3:62])[O:57][CH2:58][CH3:59]>C(Cl)Cl>[CH2:61]([O:60][P:56]([CH2:55][CH2:54][O:53][CH2:52][CH2:51][O:50][CH2:49][CH2:48][NH:47][C:10](=[O:12])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH3:13])([O:57][CH2:58][CH3:59])=[O:63])[CH3:62]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 85082Tert-butoxycarbonylalanineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86667777Diethyl 2-(2-(2-aminoethoxy)ethoxy)ethylphosphonate

Product 1

HCID 86678316(S)-tert-butyl (1-((2-(2-(2-(diethoxyphosphoryl)ethoxy)ethoxy)ethyl)amino)-1-oxopropan-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-2-((tert-butoxycarbonyl)amino)propanoic acid (1 eq) and HBTU (1.2 eq) in DCM (0.06 M) was added DIEA (3.5 eq), followed by diethyl (2-(2-(2-aminoethoxy)ethoxy)ethyl)phosphonate (1.2 eq, from example 5, step 3). The reaction was stirred at room temperature for 2 hours. The crude mixture was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-5% MeOH/DCM to give the title product as a colorless viscous oil.

Workup

  1. customThe crude mixture was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-c4c5031c4dbc4d37920c6daa207cf7eb
Source dataset
uspto-grants-2014_08
Patent number
US08808703B2

Reaction notes

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