(-)-Asparagine → HCID 22881390, compound

HRID 2297091Notes

Reaction equation

HRID 2297091 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5].C(N(CC)CC)C.[C:17]1([CH3:29])[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[C:18]=1[S:25](Cl)(=[O:27])=[O:26]>O1CCCC1.O>[CH3:29][C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[C:18]=1[S:25]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5])(=[O:26])=[O:27]

Participants

6

Reactant 3

HCID 6267(-)-AsparagineHCID 8471TriethylamineHCID 130462-Mesitylenesulfonyl chloride

Product 1

HCID 22881390HCID 22881390, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

L-Asparagine (20.0 g, 0.15M) was suspended in a mixture of tetrahydrofuran (l30 mL) and water (250 mL). Triethylamine (49 g, 0.48M) was added followed by mesitylenesulfonyl chloride (49.7 g, 0.227M), The reaction mixture became slightly exothermic and the solids dissolved over a period of 0.5 h. to yield a yellow solution. The reaction mixture was stirred for 3 h at room temperature, then washed with ether, and methylene chloride. The aqueous layer was separated, and acidified to ca. pH=1.5 with conc. HCl, during which time a thick precipitate formed. After 0.5 h. the product was filtered,washed with water and dried to yield a white solid (34 g, 72%). m.p.=193.5 - 1950C 1H NMR (DMSO) δ 2.24 (s, 3H), 2.28 (dd, 1H), 2.45 (dd, 1H), 2.55 (s, 6H, 3.98 (m, 1H), 6.88 (br s, 1H), 6.99 (s, 2H), 7.32 (br s, 1H), 7.82 (d, 2H), 12.58 (br s, 1H). Mass spectrum ESI m/z 315.2, (M+H base peak).

Workup

  1. dissolutionthe solids dissolved over a period of 0.5 h.
  2. customto yield a yellow solution
  3. washwashed with ether, and methylene chloride
  4. customThe aqueous layer was separated
  5. customduring which time a thick precipitate formed
  6. customdried

Sources & evidence

ORD record
ord-2be0f9f0c79647ab80c207e3d6c1fd21
Source dataset
uspto-grants-2002_12
Patent number
US06489333B2

Reaction notes

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