Sodium Hydroxide → HCID 69103320, compound

HRID 2220384Notes

Reaction equation

HRID 2220384 reaction equation
Cl.Cl.[NH2:3][CH2:4][C@@H:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)[OH:6].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21](O)=[O:22])=[CH:16][CH:15]=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[OH-].[Na+]>CN(C)C=O.O.C(N(CC)CC)C>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([NH:3][CH2:4][C@H:5]([OH:6])[C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[O:22])=[CH:16][CH:15]=1

Participants

9

Reactant 5

HCID 14798Sodium HydroxideHCID 74654Benzeneacetic acid, 4-bromo-HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69103521(1R)-2-amino-1-(3-pyridyl)ethanol dihydrochloride

Product 1

HCID 69103320HCID 69103320, compoundYield 81.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of (1R)-2-amino-1-(3-pyridyl)ethanol dihydrochloride (260 g), (4-bromophenyl)acetic acid (278 g), 1-hydroxybenzotriazole (175 g) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (248 g) in N,N-dimethylformamide (1.3 l) was added triethylamine (361 l) at ambient temperature for 1 hour. The mixture was stirred at room temperature overnight. To the mixture was added water (1.3 l). The mixture was poured into water (1.6 l) and basified with 24% aqueous sodium hydroxide solution. The mixture was stirred at room temperature for 5 hours. The precipitate was collected by filtration, washed with water and dried in vacuo to give 2-(4-bromophenyl)-N-[(2R)-2-hydroxy-2-(3-pyridyl)ethyl]acetamide (335 g).

Workup

  1. stirringThe mixture was stirred at room temperature for 5 hours
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-7108f1a580e448d59f1fa7615eb5d8a0
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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