Potassium Carbonate → HCID 54128034, compound

HRID 1594533Notes

Reaction equation

HRID 1594533 reaction equation
[C:1]([O:5][C:6](=[O:29])[C@@H:7]([CH:26]([CH3:28])[CH3:27])[NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][CH:20]=2)=[CH:14][CH:13]=1)(=[O:11])=[O:10])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl.[N:37]1[CH:42]=[CH:41][CH:40]=[C:39]([CH2:43]Cl)[CH:38]=1.Cl.N1C=CC=CC=1CCl>CN(C=O)C.C(OCC)(=O)C.O>[C:1]([O:5][C:6](=[O:29])[C@@H:7]([CH:26]([CH3:27])[CH3:28])[N:8]([S:9]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:20]=[CH:21][C:22]([Br:25])=[CH:23][CH:24]=2)=[CH:14][CH:13]=1)(=[O:11])=[O:10])[CH2:43][C:39]1[CH:38]=[N:37][CH:42]=[CH:41][CH:40]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 23392Picolyl chloride hydrochlorideHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 54527823HCID 54527823, compound

Product 1

HCID 54128034HCID 54128034, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-[4-(4-bromophenoxy)benzenesulfonyl]-D-valine t-butyl ester (980 mg, 2.0 mol) in 5 mL of DMF was added potassium carbonate (1.53 g, 11.1 mol), 3-picolyl chloride hydrochloride (414 mg, 2.53 mol), and Kl (67 mg, 0.4 mol). The reaction was stirred at room temperature overnight. An additional 220 mg of picolyl chloride hydrochloride was added, and the reaction was stirred for 3 h. Water (25 mL) and ethyl acetate (50 mL) were added, and the layers were separated. The ethyl acetate fraction was washed with brine, dried over MgSO4, and concentrated. The residue was purified by chromatography on silica, eluting with 35% ethyl acetate in hexane, to give 1.07g (92%) of N-[4-(4-bromophenoxy)benzenesulfonyl]-N-(pyridin-3-yl)methyl-D-valine t-butyl ester as a tan foam.

Workup

  1. stirringthe reaction was stirred for 3 h
  2. customthe layers were separated
  3. washThe ethyl acetate fraction was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica
  7. washeluting with 35% ethyl acetate in hexane

Sources & evidence

ORD record
ord-fef0d59174374a2192cf50dc698d949c
Source dataset
uspto-grants-2001_09
Patent number
USH0001992H1

Reaction notes

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