Methanesulfonyl chloride → HCID 86665755, compound

HRID 469912Notes

Reaction equation

HRID 469912 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@:9]1([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C@H:14]([CH2:15][S:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]([CH3:24])[CH:18]=2)[C@H:13]([OH:25])[C@@H:12]2[C@H:10]1[C@H:11]2[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:40][S:41](Cl)(=[O:43])=[O:42]>N1C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][C@@:9]1([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C@H:14]([CH2:15][S:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]([CH3:24])[CH:18]=2)[C@H:13]([O:25][S:41]([CH3:40])(=[O:43])=[O:42])[C@@H:12]2[C@H:10]1[C@H:11]2[C:26]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[O:27])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 67639424Di-tert-butyl (1S,2R,3S,4R,5R,6R)-2-(tert-butoxycarbonylamino)-3-[(4-fluoro-3-methyl-phenyl)sulfanylmethyl]-4-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylate

Product 1

HCID 86665755HCID 86665755, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
40 °C

Procedure

Di-tert-butyl (1S,2R,3S,4R,5R,6R)-2-(tert-butoxycarbonylamino)-3-[(4-fluoro-3-methyl-phenyl)sulfanylmethyl]-4-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylate (4.6 g, 8.10 mmol) in pyridine (60 mL) is cooled to 0° C. To this mixture is added methanesulfonyl chloride (1.88 ml, 24.31 mmol). The mixture is warmed to 40° C. and stirred for 1 hour, and cooled to ambient temperature and allowed to stir for 18 hours. The mixture is concentrated under reduced pressure to give a residue. The residue is partitioned between ethyl acetate and 1N aqueous HCl (2×50 mL). The organic layer is separated, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give the title compound (5.2 g, 8.05 mmol, 99.4% yield): MS (m/z): 643.6 (M−H).

Workup

  1. temperaturecooled to ambient temperature
  2. stirringto stir for 18 hours
  3. concentrationThe mixture is concentrated under reduced pressure
  4. customto give a residue
  5. customThe residue is partitioned between ethyl acetate and 1N aqueous HCl (2×50 mL)
  6. customThe organic layer is separated
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8d675c4fb304476d8da3d5d2a0f818e3
Source dataset
uspto-grants-2014_01
Patent number
US08629169B2

Reaction notes

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