Ammonium Chloride → HCID 86708063, compound

HRID 1524360Notes

Reaction equation

HRID 1524360 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([N:18]([CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[S:19]([C:22]1[CH:27]=[CH:26][C:25]([CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])=[CH:24][CH:23]=1)(=[O:21])=[O:20])[CH2:11][CH2:12][C:13]([F:17])([F:16])[CH2:14][OH:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:42][S:43](Cl)(=[O:45])=[O:44].[NH4+].[Cl-]>ClCCl>[CH3:42][S:43]([O:15][CH2:14][C:13]([F:16])([F:17])[CH2:12][CH2:11][C@H:10]([N:18]([S:19]([C:22]1[CH:27]=[CH:26][C:25]([CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:31])[CH3:32])=[CH:24][CH:23]=1)(=[O:20])=[O:21])[CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[CH2:9][O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2])(=[O:45])=[O:44]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 86708061HCID 86708061, compound

Product 1

HCID 86708063HCID 86708063, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the material from Step 7 (242 mg, 0.38 mmol) in dichloromethane (3.8 mL) at 0° C. were added N,N-diisopropylaethylamine (99 μL, 0.57 mmol) and methanesulfonyl chloride (33 μL, 0.417 mmol). The reaction mixture was stirred at room temperature overnight, poured into saturated aqueous NH4Cl and extracted with dichloromethane (2×). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel using EtOAc-hexanes to afford 167 mg of the title compound. LCMS (M+Na)=738.

Workup

  1. extractionextracted with dichloromethane (2×)
  2. washThe combined organics were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-43e01e052b0b4fcdabe9f79d62ffede3
Source dataset
uspto-grants-2015_07
Patent number
US09079834B2

Reaction notes

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