Diisopropylethylamine → HCID 44392223, compound

HRID 2417429Notes

Reaction equation

HRID 2417429 reaction equation
Cl.[NH2:2][C@H:3]([CH2:21][OH:22])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:13])=[CH:7][CH:6]=1.[Cl:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C@H:27]1[O:29][CH2:28]1.C(N(CC)C(C)C)(C)C>C(O)C>[Cl:23][C:24]1[CH:25]=[C:26]([C@@H:27]([OH:29])[CH2:28][NH:2][C@H:3]([CH2:21][OH:22])[CH2:4][C:5]2[CH:6]=[CH:7][C:8]([NH:11][C:12]([NH:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[O:13])=[CH:9][CH:10]=2)[CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 10898919(R)-(+)-3-Chlorostyrene oxideHCID 69817672HCID 69817672, compound

Product 1

HCID 44392223HCID 44392223, compoundYield 28.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under nitrogen, a solution of (S)-N-[4-(2-amino-3-hydroxypropyl)phenyl]-N′-phenylurea hydrochloride (150 mg), (R)-3-chlorostyrene oxide (56 mg) and N,N-diisopropylethylamine (0.17 ml) in ethanol (5 ml) was refluxed for 28 hours. The mixture was evaporated in vacuo. The residue was purified by column chromatography on silica gel (chloroform:methanol=100:1) to give N-[4-[(2S)-2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-hydroxypropyl]phenyl]-N′-phenylurea (45 mg) as a colorless form.

Workup

  1. customThe mixture was evaporated in vacuo
  2. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=100:1)

Sources & evidence

ORD record
ord-e208a1f5670c4496963b40761d24158e
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

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