Diisopropylethylamine → HCID 178462373, compound

HRID 448645Notes

Reaction equation

HRID 448645 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-a3ada0ca3b344b7d965df2966acba247
Source dataset
uspto-grants-2013_07
Patent number
US08481044B2

Reaction notes

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