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Triethylamine → 2-(2-Bromo-phenyl)-N-((4S,5S)-2,2-dimethyl-4-phenyl-[1,3]dioxan-5-yl)-acetamide

HRID 966079
Notes
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Reaction equation

HRID 966079 reaction equation
[CH3:1][C:2]1([CH3:15])[O:7][C@@H:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@@H:5]([NH2:14])[CH2:4][O:3]1.C(N(CC)CC)C.[Br:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][C:31](Cl)=[O:32]>ClCCl>[Br:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][C:31]([NH:14][C@H:5]1[CH2:4][O:3][C:2]([CH3:15])([CH3:1])[O:7][C@H:6]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:32]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 41383862-Bromophenylacetyl chlorideHCID 7061833(4S,5S)-2,2-dimethyl-4-phenyl-1,3-dioxan-5-amine

Product 1

HCID 100241572-(2-Bromo-phenyl)-N-((4S,5S)-2,2-dimethyl-4-phenyl-[1,3]dioxan-5-yl)-acetamideYield 60%

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Conditions

Temperature
25 °C

Procedure

To a solution of 250 mg (1.2 mmol) of (4S,5S)-amine 1 in dichloromethane (3 mL) was added 0.16 mL (1.2 mmol) of triethylamine followed by dropwise addition of 0.17 mL (1.2 mmol) of 2-bromophenylacetyl chloride. After stirring for ˜96 h at 25° C., the reaction mixture was concentrated under reduced pressure, and the residue was purified by column chromatography (hexanes/ethyl acetate) to yield 290 mg (60%) of the title compound.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by column chromatography (hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-39e8bfadf0f3480eb724d36ebe0fa081
Source dataset
uspto-grants-2005_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06951882B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes