Diisopropylethylamine → HCID 58005123, compound

HRID 1879259Notes

Reaction equation

HRID 1879259 reaction equation
[CH2:1]([NH:7][C@H:8]([C:13]([OH:15])=O)[C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl-].[Br:50][C:51]1[CH:52]=[C:53]([C:57]2[CH:62]=[CH:61][CH:60]=[C:59]([CH2:63][O:64][C@H:65]3[CH2:69][NH2+:68][C@H:67]([C:70]([O:72][CH3:73])=[O:71])[CH2:66]3)[CH:58]=2)[CH:54]=[CH:55][CH:56]=1>CN(C=O)C.O.CCOC(C)=O>[CH2:1]([NH:7][C@H:8]([C:13]([N:68]1[CH2:69][C@H:65]([O:64][CH2:63][C:59]2[CH:58]=[C:57]([C:53]3[CH:54]=[CH:55][CH:56]=[C:51]([Br:50])[CH:52]=3)[CH:62]=[CH:61][CH:60]=2)[CH2:66][C@H:67]1[C:70]([O:72][CH3:73])=[O:71])=[O:15])[C:9]([CH3:10])([CH3:11])[CH3:12])[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58005101HCID 58005101, compoundHCID 86637108HCID 86637108, compound

Product 1

HCID 58005123HCID 58005123, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22728543Water ethylacetateSolvent

Procedure

N-hex-5-en-1-yl-3-methyl-L-valine (1.2 eq.), DIPEA (3.7 eq.) and HATU (1.2 eq.) were sequentially added to a 0.10 M solution of (2S,4R)-4-[(3′-bromobiphenyl-3-yl)methoxy]-2-(methoxycarbonyl)pyrrolidinium chloride in DMF. The reaction mixture was stirred at RT overnight then it was diluted with H2O/EtOAc and extracted. The collected organic layers were washed with brine, dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by flash chromatography (SiO2, PE:EtOAc with EtOAc from 30 to 100%) to afford the title compound 101 as a solid (50%). 1H NMR (400 MHz, DMSO-d6, 300 K) δ 7.85 (bs, 1H), 7.69 (d, J 7.8, 1H), 7.66-7.58 (m, 3H), 7.51-7.43 (m, 2H), 7.37 (d, J 7.8, 1H), 5.76-5.64 (m, 1H), 4.97-4.87 (m, 2H), 4.63 (s, 2H), 4.45 (t, J 8.6, 1H), 4.31 (bs, 1H), 4.07 (d, J 11.7, 1H), 3.66 (s, 3H), 3.73-3.55 (m, 2H), 2.50-2.41 (m, 1H), 2.40-2.32 (m, 1H), 2.31-2.23 (m, 1H), 2.08-1.96 (m, 1H), 1.94-1.85 (m, 2H), 1.34-1.18 (m, 3H), 0.96 (s, 9H), 0.94-0.85 (m, 2H). MS (ES+) m/z 585, 587 (M+H)+.

Workup

  1. extractionextracted
  2. washThe collected organic layers were washed with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated under reduced pressure
  5. customThe residue was purified by flash chromatography (SiO2, PE:EtOAc with EtOAc from 30 to 100%)

Sources & evidence

ORD record
ord-a49d7ed76c3b477ca9b4354261f398c4
Source dataset
uspto-grants-2012_11
Patent number
US08314062B2

Reaction notes

Loading…