Diisopropylethylamine → HCID 58802454, compound

HRID 14229Notes

Reaction equation

HRID 14229 reaction equation
[CH2:1]([S:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=O)[CH:2]=[CH2:3].[NH2:14][C@H:15]([CH2:31][C:32]1[CH:37]=[C:36]([F:38])[CH:35]=[C:34]([F:39])[CH:33]=1)[C@H:16]([OH:30])[CH2:17][NH:18][C:19]1([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][CH3:29])[CH:23]=2)[CH2:21][CH2:20]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>ClCCl>[CH2:1]([S:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([NH:14][C@@H:15]([CH2:31][C:32]1[CH:33]=[C:34]([F:39])[CH:35]=[C:36]([F:38])[CH:37]=1)[C@H:16]([OH:30])[CH2:17][NH:18][C:19]1([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][CH3:29])[CH:23]=2)[CH2:21][CH2:20]1)=[O:10])[CH:2]=[CH2:3]

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 210857063-(Allylthio)benzoic acidHCID 57487391HCID 57487391, compound

Product 1

HCID 58802454HCID 58802454, compoundYield 176.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(Allylthio)benzoic acid (717 mg, 3.69 mmol), (2R,3R)-3-amino-4-(3,5-difluorophenyl)-1-{[1-(3-ethylphenyl)cyclopropyl]amino}butan-2-ol (247mg, 0.685 mmol), and HATU (Aldrich, 2.1 g, 5.54 mmol) were dissolved in dichloromethane (35 mL), at ambient temperature, and treated with diisopropylethylamine (1.6 mL, 9.225 mmol). Upon completion, the reaction mixture was concentrated and chromatographed (SiO2, 2:1 to 1:1 Hexanes: EtOAc) to give the desired compound (650 mg). (LRMS (M+H) m/z=537.8)

Workup

  1. concentrationUpon completion, the reaction mixture was concentrated
  2. customchromatographed (SiO2, 2:1 to 1:1 Hexanes: EtOAc)

Sources & evidence

ORD record
ord-f76c42c38271418a8ac69239164776bb
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

Loading…