Diisopropylethylamine → HCID 58802454, compound

HRID 349019Notes

Reaction equation

HRID 349019 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 (247 mg, 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-b31d74e1990345058198a69be62d11db
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Reaction notes

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