Ethyl Acetate → HCID 131723199, compound

HRID 843400Notes

Reaction equation

HRID 843400 reaction equation
[CH3:1][N:2]([C@H:21]([CH3:26])[C:22]([O:24][CH3:25])=[O:23])[C:3](=[O:20])[CH:4]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)[CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[F:27][C:28]([F:42])([F:41])[C:29]1[CH:30]=[C:31]([CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=1)[CH2:32]Br.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN(C=O)C>[CH3:1][N:2]([C@H:21]([CH3:26])[C:22]([O:24][CH3:25])=[O:23])[C:3](=[O:20])[CH:4]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:32][C:31]2[CH:34]=[C:35]([C:37]([F:39])([F:40])[F:38])[CH:36]=[C:29]([C:28]([F:27])([F:41])[F:42])[CH:30]=2)=[CH:15][CH:14]=1)[CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 1225733,5-Bis(trifluoromethyl)benzyl bromideHCID 69883181HCID 69883181, compound

Product 1

HCID 131723199HCID 131723199, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 2-UN-methyl-N-((R/S)-α-t-butoxycarbonylmethyl-4-hydroxyphenylacetyl)amino]-(R)-propionate 48d (1.5 g, 4.1 mmol) and 3,5-bistrifluoromethylbenzyl bromide (1.3 g, 4.2 mmol) in DMF (10 mL) was stirred at 60° C. overnight in the presence of K2CO3 (1.14 g, 8 mmol). After cooling to room temperature, EtOAc was added and the solution was washed with brine three times, dried over MgSO4, and concentrated. Purification on a silica gel column by eluting with 40% EtOAc/hexane afforded the product (1.46 g, 60%) as a solid. MS (CI—NH3): (M+H)+=592.

Workup

  1. washthe solution was washed with brine three times
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customPurification on a silica gel column
  5. washby eluting with 40% EtOAc/hexane

Sources & evidence

ORD record
ord-d4d98bbb62ef446abcbc542462a5156e
Source dataset
uspto-grants-2002_04
Patent number
US06376665B1

Reaction notes

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