Diisopropylethylamine → HCID 46911016, compound

HRID 1510242Notes

Reaction equation

HRID 1510242 reaction equation
[N+](C1C=CC([N:10]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)[C:11](=[O:13])[O-])=CC=1)([O-])=O.C(N(CC)C(C)C)(C)C.[NH2:35][C@@H:36]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH2:37][OH:38]>ClCCl>[OH:38][CH2:37][C@@H:36]([NH:35][C:11]([NH:10][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:21]=[CH:22][N:23]=[CH:24][CH:25]=2)=[CH:18][CH:19]=1)=[O:13])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1347972-Amino-2-phenylethan-1-olHCID 69076129HCID 69076129, compound

Product 1

HCID 46911016HCID 46911016, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-nitrophenyl[4-(4-pyridinyl)phenyl]carbamate (7.50 g) and N,N-diisopropylethylamine (5.84 mL) in dichloromethane (150 mL) was added (2S)-2-amino-2-phenylethanol (4.60 g) at ambient temperature and the mixture was stirred at the same temperature for 20 hours. The resulting mixture was concentrated in vacuo and then water (45 mL) and ethyl acetate (45 mL) was added to the residue. The precipitated solid was collected by filtration and washed with water (30 mL×5) to obtain yellow crystals. The crystals were triturated with ethyl acetate (30 mL) to give 1-[(1S)-2-hydroxy-1-phenylethyl]-3-[4-(4-pyridinyl)phenyl]urea (6.1 g) as a slightly yellow crystals.

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. additionwater (45 mL) and ethyl acetate (45 mL) was added to the residue
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with water (30 mL×5)
  5. customto obtain yellow crystals
  6. customThe crystals were triturated with ethyl acetate (30 mL)

Sources & evidence

ORD record
ord-c9105b03d13541729b27c72ebdabf7cd
Source dataset
uspto-grants-2012_07
Patent number
US08211919B2

Reaction notes

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