Diisopropylethylamine → HCID 178462373, compound

HRID 535202Notes

Reaction equation

HRID 535202 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([OH:8])=O)[N:3]=[N:2]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC(=CC1=2)Cl)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:43]1([O:49][C:50]([O:52][CH:53]([O:55][C:56](=[O:77])[C@@:57]([CH2:75][OH:76])([CH3:74])[CH2:58][C@H:59]([NH2:73])[CH2:60][C:61]2[CH:66]=[CH:65][C:64]([C:67]3[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=3)=[CH:63][CH:62]=2)[CH3:54])=[O:51])[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1>CN(C=O)C>[CH:43]1([O:49][C:50]([O:52][C@H:53]([O:55][C:56](=[O:77])[C@@:57]([CH2:75][OH:76])([CH3:74])[CH2:58][C@H:59]([NH:73][C:6]([C:4]2[NH:3][N:2]=[N:1][CH:5]=2)=[O:8])[CH2:60][C:61]2[CH:66]=[CH:65][C:64]([C:67]3[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=3)=[CH:63][CH:62]=2)[CH3:54])=[O:51])[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1401204-Carboxy-1,2,3-triazoleHCID 42624899O-(6-Chlorobenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphateHCID 68181297(2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid 1-cyclohexyloxycarbonyloxy-ethyl ester

Product 1

HCID 178462373HCID 178462373, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,2,3-Triazole-4-carboxylic acid (45.2 mg, 400 μmol), DIPEA (209 μL, 1.2 mmol) and HCTU (165 mg, 400 μmol) were combined in DMF (0.2 mL) and stirred for 5 minutes at room temperature. This was then combined with (2S,4R)-4-amino-5-biphenyl-4-yl-2-hydroxymethyl-2-methyl-pentanoic acid 1-cyclohexyloxycarbonyloxy-ethyl ester (193 mg, 400 μmol). The resulting mixture was stirred for 15 minutes and the reaction was quenched with AcOH. The products were purified and separated by preparative HPLC, then lyophilized to yield to yield compound ZC (20 mg; purity 95%), MS m/z [M+H]+ calc'd for C31H38N4O2, 579.27. found 579.6, and compound ZD (15 mg; purity 95%), MS m/z [M+H]+ calc'd for C31H38N4O2, 579.27. found 579.6.

Workup

  1. stirringThe resulting mixture was stirred for 15 minutes
  2. customthe reaction was quenched with AcOH
  3. customThe products were purified
  4. customseparated by preparative HPLC
  5. customto yield
  6. customto yield compound ZC (20 mg; purity 95%), MS m/z [M+H]+ calc'd for C31H38N4O2, 579.27

Sources & evidence

ORD record
ord-960cd605d1df41a8a55807818353b640
Source dataset
uspto-grants-2014_10
Patent number
US08853427B2

Reaction notes

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