Diisopropylethylamine → HCID 54338434, compound

HRID 1729090Notes

Reaction equation

HRID 1729090 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C@:4]([C:7]1[N:8]=[CH:9][C:10]2[N:11]([S:20]([CH3:23])(=[O:22])=[O:21])[C:12]3[C:17]([C:18]=2[CH:19]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3)([CH3:6])[NH2:5].[CH:25]12[CH2:34][CH:29]3[CH2:30][CH:31]([CH2:33][CH:27]([CH2:28]3)[CH:26]1[O:35][C:36](Cl)=[O:37])[CH2:32]2.C(N(C(C)C)CC)(C)C>C1COCC1>[CH3:1][O:2][C:3](=[O:24])[C@:4]([C:7]1[N:8]=[CH:9][C:10]2[N:11]([S:20]([CH3:23])(=[O:22])=[O:21])[C:12]3[C:17]([C:18]=2[CH:19]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3)([CH3:6])[NH:5][C:36]([O:35][CH:26]1[CH:25]2[CH2:34][CH:29]3[CH2:30][CH:31]([CH2:33][CH:27]1[CH2:28]3)[CH2:32]2)=[O:37]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 108785372-adamantyl ChloroformateHCID 54211748HCID 54211748, compound

Product 1

HCID 54338434HCID 54338434, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 2-[9-(methylsulfonyl)-β-carbolin-3-yl]-alanine methylester (0.5 g, 1.4 mmol) in THF (10 mL) was added 2-adamantyloxycarbonyl chloride (345 rag, 1.7 mmol) and the solution was treated with diisopropyl ethylamine (219 mg, 1.7 mmol) in THF (5 mL). The reaction mixture was stirred for 4 hours at room temperature, evaporated in vacuum and partitioned between ethyl acetate (100 mL) and water (50 mL). The organic layer was separated,washed successively with 7.5% citric acid solution (50 mL), 8% NaHCO3 solution (50 mL) and then dried over Na2SO4. The solvent was evaporated in vacuum and N-(2-adamantyloxy-carbonyl)-2-[9-(methylsulfonyl)-β-carbolin-3-yl]-alanine methylester was isolated as a yellow oil which solidified upon drying(0.73 g, 97.7%).

Workup

  1. customevaporated in vacuum
  2. custompartitioned between ethyl acetate (100 mL) and water (50 mL)
  3. dry with materialdried over Na2SO4
  4. customThe solvent was evaporated in vacuum

Sources & evidence

ORD record
ord-d258563f8b1848adb21822d41bdb624d
Source dataset
uspto-grants-1994_07
Patent number
US05331006

Reaction notes

Loading…