Dichloromethane → HCID 86705508, compound

HRID 2279512Notes

Reaction equation

HRID 2279512 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:10][OH:11])[CH:5]=[CH:6][C:7]=1[F:8].C(Cl)Cl.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>O>[CH3:23][S:24]([O:11][CH2:10][C@@H:9]([NH:12][C:13]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:19])[C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=1)(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 86705509HCID 86705509, compound

Product 1

HCID 86705508HCID 86705508, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (S)-tert-butyl 1-(3-chloro-4-fluorophenyl)-2-hydroxyethylcarbamate (0.75 g, 2.59 mmol) and DCM (15 mL) at RT was added TEA (0.541 mL, 3.88 mmol) and MsCl (0.210 mL, 2.72 mmol). The reaction was stirred at RT for 1 h then poured into water and extracted with DCM. The combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH (500:5) to afford 0.8 g (84%) of (S)-2-(tert-butoxycarbonylamino)-2-(3-chloro-4-fluorophenyl)ethyl methanesulfonate (224).

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by SiO2 chromatography
  6. washeluting with DCM/MeOH (500:5)

Sources & evidence

ORD record
ord-2f15ecfe63044eb2ac0554f86de864d6
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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