4-Chlorobenzenesulfonyl chloride → HCID 25263461, compound

HRID 2242340Notes

Reaction equation

HRID 2242340 reaction equation
[CH3:1][C:2]([C@H:5]([NH2:8])[CH2:6][OH:7])([CH3:4])[CH3:3].C(N(CC)CC)C.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>C(Cl)Cl>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([NH:8][C@H:5]([CH2:6][OH:7])[C:2]([CH3:4])([CH3:3])[CH3:1])(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 2734079(2S)-2-Amino-3,3-dimethyl-1-butanol

Product 1

HCID 25263461HCID 25263461, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of S-tert-leucinol (0.20 g, 1.70 mmol), triethylamine (0.19 g, 1.87 mmol) and methylene chloride (10 mL) at 0° C., was added a solution of 4-chloro benzenesulfonyl chloride (0.36 g, 1.70 mmol) in CH2Cl2 (5 mL). After 15 minutes the ice bath was removed and the reaction allowed to reach 25° C. After 16 hours, the reaction was quenched by pouring into saturated sodium bicarbonate solution (20 mL) and additional methylene chloride (15 mL). The organic phase was separated and washed sequentially with 1N HCl solution (20 mL), distilled water and brine, dried over MgSO4 and evaporated to give the desired product as a white solid, mp 128-130° C. (0.46 g, 94%). MS (+APCI) 292.06 ([M+H]+). Anal. Calc'd for C12H18ClNO3S: C, 49.39; H, 6.22; N, 4.80. Found: C, 49.40; H, 6.17; N, 4.79.

Workup

  1. customAfter 15 minutes the ice bath was removed
  2. customto reach 25° C
  3. customthe reaction was quenched
  4. additionby pouring into saturated sodium bicarbonate solution (20 mL) and additional methylene chloride (15 mL)
  5. customThe organic phase was separated
  6. washwashed sequentially with 1N HCl solution (20 mL)
  7. distillationdistilled water and brine
  8. dry with materialdried over MgSO4
  9. customevaporated

Sources & evidence

ORD record
ord-de92cd0e324c4bf6a2220512d23b4b36
Source dataset
uspto-grants-2010_03
Patent number
US07671075B2

Reaction notes

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