Sodium Bicarbonate → [(S)-1-((3S,4S,7R)-2-Pyridinesulfonyl-3-hydroxy-7-methyl-azepan-4-ylcarbamoyl)-3-methyl-butyl)-carbamic acid tert-butyl ester

HRID 229808Notes

Reaction equation

HRID 229808 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7](Cl)(=[O:9])=[O:8].[C:11]([O:15][C:16](=[O:35])[NH:17][C@H:18]([C:23](=[O:34])[NH:24][C@H:25]1[CH2:31][CH2:30][C@@H:29]([CH3:32])[NH:28][CH2:27][C@@H:26]1[OH:33])[CH2:19][CH:20]([CH3:22])[CH3:21])([CH3:14])([CH3:13])[CH3:12].C(=O)(O)[O-].[Na+]>C(Cl)Cl.O.CCOC(C)=O>[C:11]([O:15][C:16](=[O:35])[NH:17][C@H:18]([C:23](=[O:34])[NH:24][C@H:25]1[CH2:31][CH2:30][C@@H:29]([CH3:32])[NH:28][CH:27]([S:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)(=[O:9])=[O:8])[C@H:26]1[OH:33])[CH2:19][CH:20]([CH3:22])[CH3:21])([CH3:13])([CH3:14])[CH3:12]

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 3787675Pyridine-2-sulfonyl ChlorideHCID 58665057[(S)-1-((3S,4S,7R)-3-hydroxy-7-methyl-azepan-4-ylcarbamoyl)-3-methyl-butyl]-carbamic acid tert-butyl ester

Product 1

HCID 69001186[(S)-1-((3S,4S,7R)-2-Pyridinesulfonyl-3-hydroxy-7-methyl-azepan-4-ylcarbamoyl)-3-methyl-butyl)-carbamic acid tert-butyl esterYield 104.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Pyridine sulfonyl chloride (0.71 g, 0.4 mmol) was added to a solution of [(S)-1-((3S,4S,7R)-3-hydroxy-7-methyl-azepan-4-ylcarbamoyl)-3-methyl-butyl]-carbamic acid tert-butyl ester (0.126 g, 0.344 mmol), sodium bicarbonate (0.87 g, 1.03 mmol) in CH2Cl2 (3 ml) and H2O (2 ml) and was stirred at RT for 30 minutes. The reaction mixture was diluted with EtOAc (100 ml), washed with H2O, brine, dried with magnesium sulfate, filtered, concentrated in vacuo by rotary evaporation, and chromatographed (silica gel, 3% MeOH/CH2Cl2) to yield the title compound (0.180 g, 70%): 1H NMR: 8.68 (m, 1H), 8.05 (1H, d), 7.92 (1H, dd), 7.50 (1H, dd), 6.66 (1H, bd), 4.95-4.88 (dd), 4.20-3.87 (m, 3H), 3.65 (1H, bs), 3.40 (1H, d), 1.94-1.57 (m, 4H), 1.45-1.38 (m, 6H), 1.14 (3H, dd), 0.94 (6H, dd); Electrospray mass spec: M+H+=499.0

Workup

  1. washwashed with H2O, brine
  2. dry with materialdried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo by rotary evaporation
  5. customchromatographed (silica gel, 3% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-0da7579e34ba4db3ab25c985a929e689
Source dataset
uspto-grants-2009_07
Patent number
US07563784B2

Reaction notes

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