Triethylamine → N-[(1R,2R)-2-Amino-1,2-diphenylethyl]-2,4,6-tris(1-methylethyl)benzenesulfonamide

HRID 1751915Notes

Reaction equation

HRID 1751915 reaction equation
[C:1]1([C@@H:7]([NH2:16])[C@@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH:24]([C:27]1[CH:32]=[C:31]([CH:33]([CH3:35])[CH3:34])[CH:30]=[C:29]([CH:36]([CH3:38])[CH3:37])[C:28]=1[S:39](Cl)(=[O:41])=[O:40])([CH3:26])[CH3:25]>ClCCl>[NH2:16][C@H:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C@H:8]([NH:9][S:39]([C:28]1[C:29]([CH:36]([CH3:37])[CH3:38])=[CH:30][C:31]([CH:33]([CH3:35])[CH3:34])=[CH:32][C:27]=1[CH:24]([CH3:26])[CH3:25])(=[O:41])=[O:40])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 810422,4,6-Tris(1-methylethyl)benzenesulfonyl chlorideHCID 2724998(1R,2R)-(+)-1,2-Diphenylethylenediamine

Product 1

HCID 12165386N-[(1R,2R)-2-Amino-1,2-diphenylethyl]-2,4,6-tris(1-methylethyl)benzenesulfonamideYield 96.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

(1R,2R)-1,2-Diphenyl-ethane-1,2-diamine (1.0 g) was dissolved in dichloromethane (20 mL), and then triethylamine (0.66 mL) added and the mixture was cooled to 5° C. (internal). 2,4,6-Triisopropyl-benzenesulfonyl chloride (1.21 g) was dissolved in dichloromethane (10 mL) and then added to the diamine mixture over 30 minutes, while maintaining the temperature between 7-10 ° C. The cooling bath was removed and the resulting mixture was stirred at 25° C. for 4 hours and the solvent was evaporated. The resulting residue was suspended in hexanes (100 mL) and washed with warm water (42° C., 3×100 mL). The hexane layer was separated, dried over Na2SO4, filtered, and evaporated to provide the product (1.85 g). 1HNMR (400 MHz, CDCl3): δ(ppm) 7.20-7.15 (m, 3H), 7.05-6.94 (m, 7H), 6.84-6.80 (m, 2H), 6.09 (br-s,1H), 4.49 (d, 1H), 3.99-3.91 (m, 3H), 2.87-2.79 (m, 1H), 1.21 (d, 6H), 1.17 (d, 6H), 1.08 (d, 6H). LC/MS: 479 (m/z).

Workup

  1. temperaturewhile maintaining the temperature between 7-10 ° C
  2. customThe cooling bath was removed
  3. customthe solvent was evaporated
  4. washwashed with warm water (42° C., 3×100 mL)
  5. customThe hexane layer was separated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-dbded7fc4c484a3197c0ea42919998fd
Source dataset
uspto-grants-2015_10
Patent number
US09162963B2

Reaction notes

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