Diisopropylethylamine → HCID 69817657, compound

HRID 2417435Notes

Reaction equation

HRID 2417435 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.C(N(CC)C(C)C)(C)C.[CH2:32]([O:39][C:40]1[CH:50]=[CH:49][C:43]([O:44][CH2:45][C@@H:46]2[CH2:48][O:47]2)=[CH:42][CH:41]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(O)C>[CH2:32]([O:39][C:40]1[CH:41]=[CH:42][C:43]([O:44][CH2:45][C@@H:46]([OH:47])[CH2:48][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:49][CH:50]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 11817709(2S)-2-{[4-(benzyloxy)phenoxy]methyl}oxiraneHCID 69817672HCID 69817672, compound

Product 1

HCID 69817657HCID 69817657, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-[4-[(2S)-2-amino-3-hydroxypropyl]phenyl]-N′-phenylurea hydrochloride (222 mg) in ethanol (5.0 ml) were added successively N,N-diisopropylethylamine (264 μl) and (2S)-2-[[4-(benzyloxy)phenoxy)methyl]oxirane (212 mg) and the solution was refluxed for 13.5 hours. After cooling to room temperature, the precipitates were collected by filtration, washed with ethanol, and dried under reduced pressure to give N-[4-[(2S)-2-[[(2S)-3-[4-(benzyloxy)phenoxy]-2-hydroxypropyl]amino]-3-hydroxypropyl]phenyl]-N′-phenylurea (166 mg) as a white solid.

Workup

  1. temperaturethe solution was refluxed for 13.5 hours
  2. filtrationthe precipitates were collected by filtration
  3. washwashed with ethanol
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-f7580eed6e2c4ee59cf36b1aa5041fb5
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

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