Diisopropylethylamine → HCID 178459929, compound

HRID 535161Notes

Reaction equation

HRID 535161 reaction equation
[C:1]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@@H:8]([NH:16][C:17]([O:19]C(C)(C)C)=O)[CH2:9][C@@H:10]([CH2:14][OH:15])[C:11]([OH:13])=[O:12])=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.[C:39](=[O:48])([O:44][CH:45]([CH3:47])[CH3:46])[O:40][CH:41](Cl)[CH3:42].[NH:49]1[CH:53]=[C:52](C(O)=O)[N:51]=[N:50]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CC(N(C)C)=O>[CH:45]([O:44][C:39]([O:40][CH:41]([O:13][C:11](=[O:12])[C@H:10]([CH2:14][OH:15])[CH2:9][C@H:8]([NH:16][C:17]([C:53]1[NH:49][N:50]=[N:51][CH:52]=1)=[O:19])[CH2:7][C:4]1[CH:3]=[CH:2][C:1]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:6][CH:5]=1)[CH3:42])=[O:48])([CH3:47])[CH3:46]

Participants

8

Reactant 5

HCID 81531Diisopropylethylamine2×HCID 1401204-Carboxy-1,2,3-triazoleHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 117895851-Chloroethyl 1-methylethyl carbonateHCID 68181177(2S,4S)-5-Biphenyl-4-yl-4-t-butoxycarbonylamino-2-hydroxymethyl-pentanoic acid

Product 1

HCID 178459929HCID 178459929, compoundYield 9.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 31374DimethylacetamideSolvent

Procedure

(2S,4S)-5-Biphenyl-4-yl-4-t-butoxycarbonylamino-2-hydroxymethyl-pentanoic acid (50 mg, 120 μmol, 1.0 eq.), DMA (1 mL), DIPEA (0.13 mL) and 1-chloroethyl isopropyl carbonate (83 mg, 0.5 mmol, 4.0 eq.) were combined. The reaction vessel was capped and microwaved at 80° C. for 2 hours. The mixture was dried under vacuum, dissolved in MeCN (2 mL), and combined with 4 M of HCl in dioxane (500 μL). The resulting mixture was stirred at room temperature for 30 minutes. The precipitate was filtered and discarded, and the filtrate containing the intermediate was concentrated down and submitted to the next step. 1,2,3-Triazole-4-carboxylic acid (14 mg, 120 μmol, 0.5 eq.) and HATU (48 mg, 120 μmol, 1.0 eq) were dissolved in DMF (1 mL) and the resulting solution was stirred for 5 minutes, followed by the addition of DIPEA (44 μL) and the intermediate from last step. The mixture was stirred for 5 minutes. The reaction was quenched with water and the product dried under vacuum. The product was then purified by preparative HPLC to yield the title compound (6 mg; purity 95%). MS m/z [M+H]+ calc'd for C27H32N4O7, 525.23. found 525.4.

Workup

  1. customThe reaction vessel was capped
  2. custommicrowaved at 80° C. for 2 hours
  3. customThe mixture was dried under vacuum
  4. dissolutiondissolved in MeCN (2 mL)
  5. filtrationThe precipitate was filtered
  6. additionthe filtrate containing the intermediate
  7. concentrationwas concentrated down and
  8. stirringthe resulting solution was stirred for 5 minutes
  9. stirringThe mixture was stirred for 5 minutes
  10. customThe reaction was quenched with water
  11. customthe product dried under vacuum
  12. customThe product was then purified by preparative HPLC

Sources & evidence

ORD record
ord-ddc0e0705359427cab27066f287ab0fa
Source dataset
uspto-grants-2014_10
Patent number
US08853427B2

Reaction notes

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