Diisopropylethylamine → HCID 178473536, compound

HRID 2212246Notes

Reaction equation

HRID 2212246 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[NH:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)=S)[CH3:2].Cl.[O:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=[C:17]1[CH:25]([OH:38])[CH:26]([NH:29][C:30](=[O:37])[CH:31]([NH2:36])[CH2:32][CH:33]([CH3:35])[CH3:34])[CH2:27][CH3:28].C(N(C(C)C)CC)(C)C.[I-].ClC1C=CC=C[N+]=1C>ClCCl>[CH2:1]([O:3][C:4](=[O:14])[N:5]=[C:6]([NH:36][C@H:31]([C:30](=[O:37])[NH:29][C@H:26]([C:25]([C:17]1[O:16][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=1)=[O:38])[CH2:27][CH3:28])[CH2:32][CH:33]([CH3:34])[CH3:35])[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)[CH3:2]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 2824559Ethyl (morpholin-4-ylcarbonothioyl)carbamateHCID 21962742HCID 21962742, compound

Product 1

HCID 178473536HCID 178473536, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(Morpholine-4-carbothioyl)carbamic acid ethyl ester (55 mg, 0.25 mmol), 2-amino-4-methylpentanoic acid [1-(benzoxazol-2-ylhydroxymethyl)propyl]amide hydrochloride (90 mg, 0.25 mmol), and diisopropylethylamine (0.13 mL, 0.76 mmol) were dissolved in dichloromethane (5 mL). 2-Chloro-1-methylpyridinium iodide (84 mg, 0.33 mmol) was added and the reaction mixture was stirred at ambient temperature over night. After dilution with ethyl acetate (100 mL), the solution was washed with sat. aq. NaHCO3, and brine, dried with MgSO4 and evaporated under vacuum. The residue was dissolved in dichloromethane (10 mL) and Dess-Martin periodinane (400 mg) was added. The reaction mixture was stirred at ambient temperature for 1 h. After dilution with ethyl acetate (100 mL), the solution was washed with a 0.26 M solution of Na2S2O3 in sat. aqu. NaHCO3, then with sat. aq. NaHCO3, and brine, dried with MgSO4 and evaporated under vacuum. After purification by flash chromatography on silica gel, the title compound was obtained as yellowish glass (10 mg, 0.020 mmol). MS: (M+H)+ 502.

Workup

  1. washAfter dilution with ethyl acetate (100 mL), the solution was washed with sat. aq. NaHCO3, and brine
  2. dry with materialdried with MgSO4
  3. customevaporated under vacuum
  4. dissolutionThe residue was dissolved in dichloromethane (10 mL)
  5. additionDess-Martin periodinane (400 mg) was added
  6. stirringThe reaction mixture was stirred at ambient temperature for 1 h
  7. washAfter dilution with ethyl acetate (100 mL), the solution was washed with a 0.26 M solution of Na2S2O3 in sat. aqu
  8. dry with materialNaHCO3, then with sat. aq. NaHCO3, and brine, dried with MgSO4
  9. customevaporated under vacuum
  10. customAfter purification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-2f8fb33046c747e28e8b9420a185a12a
Source dataset
uspto-grants-2006_09
Patent number
US07101880B2

Reaction notes

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