Triethylamine → HCID 58017457, compound

HRID 1518207Notes

Reaction equation

HRID 1518207 reaction equation
[NH2:1][C@@H:2]([C:7]([OH:9])=[O:8])[C:3]([CH3:6])([CH3:5])[CH3:4].[CH3:10][O:11][C:12]1[CH:13]=[C:14]([S:18](Cl)(=[O:20])=[O:19])[CH:15]=[CH:16][CH:17]=1.C(N(CC)CC)C>O1CCOCC1.O>[CH3:10][O:11][C:12]1[CH:13]=[C:14]([S:18]([NH:1][C@@H:2]([C:7]([OH:9])=[O:8])[C:3]([CH3:6])([CH3:5])[CH3:4])(=[O:20])=[O:19])[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27375043-Methoxybenzenesulfonyl chlorideHCID 6950340D-tert-leucine

Product 1

HCID 58017457HCID 58017457, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

D-tert-leucine (3 g, 22.9 mmol), 3-methoxy benzenesulfonyl chloride (4.68 g, 22.6 mmol) and triethylamine (6.4 ml, 45.7 mmol) are stirred in dioxane-water (1:1, 60 ml) at ambient temperature for 20 minutes. The reaction mixture is concentrated in vacuo and the residue is re-dissolved in Ethyl Acetate and washed with 1 N HCl. The organics are separated and washed with brine. The organic layer is dried over MgSO4 and concentrated to afford the title compound as a white solid (6.36 g, 92% yield). 1H-NMR (CDCl3, 400 MHz): δ 7.49 (d, 1H, J=8), 7.39 (s, 1H), 7.32 (t, 1H, J=8.11), 7.00 (m, 1H), 5.67 (d, 1H, J=12), 3.86 (s, 3H), 3.42 (d, 2H, J=8), 1.01 (s, 9H). Mass spectrum (302.0; M+1, 300.0; M−1).

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. dissolutionthe residue is re-dissolved in Ethyl Acetate
  3. washwashed with 1 N HCl
  4. customThe organics are separated
  5. washwashed with brine
  6. dry with materialThe organic layer is dried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ac07a9d0d21544b49a52856b6419337b
Source dataset
uspto-grants-2012_07
Patent number
US08232427B2

Reaction notes

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