Methanesulfonyl chloride → HCID 59113179, compound

HRID 276269Notes

Reaction equation

HRID 276269 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH2:20][OH:21])[C@H:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>N1C=CC=CC=1.CCOC(C)=O>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH2:20][O:21][S:23]([CH3:22])(=[O:25])=[O:24])[C@H:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])[CH3:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 59113072benzyl ((2R,3R)-3-(tert-butoxy)-1-hydroxybutan-2-yl)carbamate

Product 1

HCID 59113179HCID 59113179, compoundYield 100.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1R,2R)-N-(benzyloxycarbonyl)-1-(hydroxymethyl)-2-(tert-butoxy)propanamine (1.6 g, 5.4 mmol) in anh. pyridine (30 mL) at 4° C. was added methanesulfonyl chloride (0.75 mL, 9.7 mmol) dropwise. The reaction was stirred for 5.5 h, then was diluted with EtOAc (200 mL) and washed with a 1N HCl solution (4×200 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure to yield (1R,2R)-N-(benzyloxycarbonyl)-1-(methanesulfonyloxymethyl)-2-(tert-butoxy)propanamine as an oil (2.03 g, 100%): TLC (25% EtOAc/hex) Rf0.31.

Workup

  1. washwashed with a 1N HCl solution (4×200 mL)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-64048efeedb04542a5227f6c22ac3205
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

Loading…