Phenylmethanesulfonyl chloride → HCID 44284880, compound

HRID 1978287Notes

Reaction equation

HRID 1978287 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:14]([NH:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:15])[CH2:3][C:4](=[O:13])[O:5]CC1C=CC=CC=1.[CH2:32]([S:39](Cl)(=[O:41])=[O:40])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C(OCC)(=O)C.C(Cl)Cl>[C:33]1([CH2:32][S:39]([NH:1][C@H:2]([C:14]([NH:16][CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:15])[CH2:3][C:4](=[O:13])[OH:5])(=[O:41])=[O:40])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 2

HCID 74740Phenylmethanesulfonyl chlorideHCID 14444045HCID 14444045, compound

Product 1

HCID 44284880HCID 44284880, compoundYield 54.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The keto amide (8) (109 mg, 0.24 mmol) was dissolved in ethyl acetate (5 mL) and cooled in an ice bath. Dry HCl gas was bubbled through until the solution was saturated and then the solution was stirred at r.t. until the starting material had been consumed as indicated by tlc (˜30 min). The solvent was removed under reduced pressure. The residue (22) was dissolved in dry CH2Cl2 (5 mL) and triethylamine (61 mg, 84 μL) added. The solution was then added dropwise to a solution of benzyl sulfonyl chloride (46 mg, 0.24 mmol) in dry CH2Cl2 (5 mL) cooled in an ice bath. The resulting solution was allowed to stir at r.t. for 16 h. It was washed with 1M HCl, 5% sodium bicarbonate solution and saturated brine, then dried (MgSO4) and the solvent removed under reduced pressure to yield the product as a white solid (51 mg, 42%): mp 128-130° C. 1H NMR (CDCl3) δ2.61 & 2.99 (ABX, 2H, β-CH2), 2.86 (t, 2H, CH2Ph), 3.57 (m, 2H, NH—CH2), 4.74 (m, 1H, α-CH), 5.14 (2×s, 4H, benzyl CH2's), 6.53 & 6.74 (m, 2H, NH's), 7.29 (m, 15H, aromatic CH's); FABMS m/e 509 (M++1).

Workup

  1. temperaturecooled in an ice bath
  2. customDry HCl gas was bubbled through until the solution
  3. customhad been consumed
  4. customas indicated by tlc (˜30 min)
  5. customThe solvent was removed under reduced pressure
  6. dissolutionThe residue (22) was dissolved in dry CH2Cl2 (5 mL)
  7. additiontriethylamine (61 mg, 84 μL) added
  8. temperaturecooled in an ice bath
  9. stirringto stir at r.t. for 16 h
  10. washIt was washed with 1M HCl, 5% sodium bicarbonate solution and saturated brine
  11. dry with materialdried (MgSO4)
  12. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-905fbb2022dd4d108374c5a36c1f078a
Source dataset
uspto-grants-2001_05
Patent number
US06235929B1

Reaction notes

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