Diisopropylethylamine → HCID 117607807, compound

HRID 58808Notes

Reaction equation

HRID 58808 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[OH:34][C@H:35]([C:55]1[CH:60]=[CH:59][C:58]([O:61][CH3:62])=[CH:57][CH:56]=1)[C@H:36]([NH:40][C:41](=[O:54])[C@@H:42]([NH:44][C:45](=[O:53])[CH2:46][N:47]1[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1)[CH3:43])[C:37](O)=[O:38].[NH2:63][C@@H:64]([CH2:71][CH:72]1[CH2:76][CH2:75][CH2:74][CH2:73]1)[C:65]([C@@:67]1([CH3:70])[CH2:69][O:68]1)=[O:66]>CN(C=O)C>[CH:72]1([CH2:71][C@H:64]([NH:63][C:37](=[O:38])[C@@H:36]([NH:40][C:41](=[O:54])[C@@H:42]([NH:44][C:45](=[O:53])[CH2:46][N:47]2[CH2:52][CH2:51][O:50][CH2:49][CH2:48]2)[CH3:43])[C@H:35]([OH:34])[C:55]2[CH:60]=[CH:59][C:58]([O:61][CH3:62])=[CH:57][CH:56]=2)[C:65]([C@@:67]2([CH3:70])[CH2:69][O:68]2)=[O:66])[CH2:73][CH2:74][CH2:75][CH2:76]1

Participants

6

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 117607800HCID 117607800, compoundHCID 117607802HCID 117607802, compound

Product 1

HCID 117607807HCID 117607807, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sequentially HATU (1.84 g, 4.80 mmol) and DIEA (0.63 mL, 20 mmol) were added to a 0° C. solution of (2S,3R)-3-hydroxy-3-(4-methoxyphenyl)-2-((S)-2-(2-morpholinoacetamido)propanamido)propanoic acid (1.65 g, 4.00 mmol) and (S)-2-amino-3-cyclopentyl-1-((R)-2-methyloxiran-2-yl)propan-1-one (1.2 g, 4.0 mmol) in DMF (30 mL). The reaction mixture was allowed to warm to ambient temperature and stirred for 30 min. The mixture was concentrated and the residue was purified by flash column chromatography on silica gel (petroleum ether/EtOAc=2:1 to EtOAc) to afford (2S,3R)-N-((S)-3-cyclopentyl-1-((R)-2-methyloxiran-2-yl)-1-oxopropan-2-yl)-3-hydroxy-3-(4-methoxyphenyl)-2-((S)-2-(2-morpholinoacetamido)propanamido)propanamide (1.45 g, 61% yield) as a colorless solid. 1H NMR (300 MHz, CDCl3): δ 7.40 (d, J=5.7 Hz, 1H), 7.32-7.22 (m, 2H), 7.06-6.99 (m, 2H), 6.82 (d, J=8.7 Hz, 2H), 5.26-5.21 (m, 1H), 4.68-4.60 (m, 2H), 4.58-4.39 (m, 2H), 4.01-3.85 (m, 1H), 3.81 (s, 3H), 3.74-3.72 (m, 4H), 3.25 (d, J=4.8 Hz, 1H), 2.99-2.85 (m, 2H), 2.53-2.39 (m, 4H), 1.74-1.61 (m, 8H), 1.53 (s, 3H), 1.33 (d, J=6.9 Hz, 3H), 1.28-1.20 (m, 3H). MS(EI) for C30H44N4O8, found 589.3 (MH)+.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by flash column chromatography on silica gel (petroleum ether/EtOAc=2:1 to EtOAc)

Sources & evidence

ORD record
ord-6c470cf12a0647f0815d1282b6ee86ed
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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