Hydrochloric Acid → HCID 86587678, compound

HRID 2415425Notes

Reaction equation

HRID 2415425 reaction equation
CC12C(C)(C)C(C([O:13][CH2:14][C@@:15]([OH:32])([CH3:31])[C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[C:21]([C:27]([F:30])([F:29])[F:28])[CH:20]=3)=[O:17])=O)(CC1)OC2=O.C(N(CC)CC)C.[CH3:41][S:42](Cl)(=[O:44])=[O:43].Cl>ClCCl.C(OCC)(=O)C>[CH3:41][S:42]([O:13][CH2:14][C@@:15]([OH:32])([CH3:31])[C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[C:21]([C:27]([F:30])([F:29])[F:28])[CH:20]=1)=[O:17])(=[O:44])=[O:43]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 69417516HCID 69417516, compound

Product 1

HCID 86587678HCID 86587678, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

439 mg of chiral diol (5C) of Example 22 was dissolved in 20 ml of dichloromethane. The solution was cooled to 0° C. (ice). 170 mg of triethylamine was added. 174 mg of methanesulfonyl chloride was dissolved in 5 ml of dichloromethane and slowly added to the diol solution. After the addition was completed, the mixture was allowed to warm to room temperature. After 25 minutes at room temperature, the reaction mixture was analyzed with HPLC; there was still 27% of diol present. Next 70 mg of methanesulfonyl chloride was added. After 10 minutes at room temperature, the reaction was completed. 60 ml of ethyl acetate and 60 ml of 0.5 N aqueous HCl were added. The organic layer was washed subsequently with 60 ml of water and 60 ml of saturated NaHCO3, dried (Na2SO4), filtrated and evaporated to dryness. Purification of the residue by column chromatography (Merck silica gel 60; eluens: ethyl acetate) afforded the title compound as a green/black oil. Isolated yield: 473 mg. 1H-NMR confirmed the expected structure (2S-enantiomer). HPLC: 94% purity.

Workup

  1. additionAfter the addition
  2. temperatureto warm to room temperature
  3. waitAfter 10 minutes at room temperature
  4. washThe organic layer was washed subsequently with 60 ml of water and 60 ml of saturated NaHCO3
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltrated
  7. customevaporated to dryness
  8. customPurification of the residue by column chromatography (Merck silica gel 60; eluens: ethyl acetate)

Sources & evidence

ORD record
ord-546db11723df4635ae5725b2abe0e2f0
Source dataset
uspto-grants-2004_11
Patent number
US06818766B2

Reaction notes

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