Potassium Carbonate → HCID 68019351, compound

HRID 456254Notes

Reaction equation

HRID 456254 reaction equation
[NH2:1][C@@H:2]1[CH2:6][N:5]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:4][C@H:3]1[N:14]([CH3:27])[S:15]([C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)(=[O:17])=[O:16].C([O-])([O-])=O.[K+].[K+].[C:34]([N:41](N)[CH2:42][CH:43]=O)([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35].[BH3-]C#N.[Na+]>CO.[Cl-].[Cl-].[Zn+2]>[CH2:7]([N:5]1[CH2:4][C@@H:3]([N:14]([CH2:27][CH2:7][CH:8]([CH3:13])[CH3:9])[S:15]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)(=[O:16])=[O:17])[C@H:2]([NH:1][CH2:43][CH2:42][NH:41][C:34](=[O:35])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:6]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 67773917HCID 67773917, compoundHCID 86666333HCID 86666333, compound

Product 1

HCID 68019351HCID 68019351, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of N-[(3R,4R)-4-amino-1-benzylpyrrolidin-3-yl]-N-methyl-4-nitrobenzenesulfonamide (692 mg, 1.5 mmol) in MeOH was added K2CO3 (405 mg, 3 mmol) and the mixture was stirred for 0.5 hour at room temperature. To this mixture, Boc-amino glycinal (1.8 mmol) was added following by addition of a solution of NaBH3CN (111 mg, 1.8 mmol) and ZnCl2 (0.6 eq) in MeOH at room temperature. The reaction mixture was stirred at room temperature overnight, quenched with 1N aqueous NaOH, extracted with CHCl3, the combined organic extracts were dried with Na2SO4 and evaporated. The residue was purified by column chromatography on silica gel eluting with 2-5% MeOH in CHCl3 giving the desired product.

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. customquenched with 1N aqueous NaOH
  3. extractionextracted with CHCl3
  4. dry with materialthe combined organic extracts were dried with Na2SO4
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel eluting with 2-5% MeOH in CHCl3 giving the desired product

Sources & evidence

ORD record
ord-b9db577e22c148dbad63780be381e263
Source dataset
uspto-grants-2013_07
Patent number
US08497383B2

Reaction notes

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