Dichloromethane → HCID 131729711, compound

HRID 1922308Notes

Reaction equation

HRID 1922308 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@H:6]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:5]2.[N:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24]O)[CH:19]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[Cl:59]CCl>>[ClH:59].[N:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][O:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[CH2:7][C@H:6]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:5]3)[CH:19]=1

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 75103-PyridinemethanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 66857149(S)-N-(5-hydroxy-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

Product 1

HCID 131729711HCID 131729711, compound

Procedure

A mixture of N-[(2S)-5-hydroxy-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide (120 mg, 0.470 mmol, Description 3) and 3-pyridinylmethanol (51.3 mg, 0.470 mmol) in dichloromethane (10 ml) was stirred under argon at room temperature. Triphenylphosphine (123 mg, 0.470 mmol) and diisopropyl azodicarboxylate (0.091 ml, 0.470 mmol) were then successively added. The resulting mixture was stirred at room temperature under argon for 16 hours. The reaction mixture was washed with water, dried over sodium sulphate, filtered and evaporated. The desired product was purified by column chromatography on silica eluting with 1 to 99% ethyl acetate in n-pentane and then by SCX column eluting with 1M ammonia in methanol solution to give the title compound as a white solid. The free base solid was dissolved in methanol and treated with ethereal hydrochloride to give the HCl salt (64 mg).

Workup

  1. stirringThe resulting mixture was stirred at room temperature under argon for 16 hours
  2. washThe reaction mixture was washed with water
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe desired product was purified by column chromatography on silica eluting with 1 to 99% ethyl acetate in n-pentane
  7. washby SCX column eluting with 1M ammonia in methanol solution

Sources & evidence

ORD record
ord-3cf94880f38a495bb4fe5b6c02f72c20
Source dataset
uspto-grants-2012_05
Patent number
US08173820B2

Reaction notes

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