4-Nitrobenzenesulfonyl chloride → N-{2-[(3S)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-{[(4-nitrophenyl)sulfonyl]amino}butyl]phenyl}-Nalpha-(methoxycarbonyl)-beta-phenyl-L-phenylalaninamide

HRID 714131Notes

Reaction equation

HRID 714131 reaction equation
[NH2:1][C@H:2]([CH2:33][O:34][Si:35]([C:48]([CH3:51])([CH3:50])[CH3:49])([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12](=[O:32])[C@H:13]([CH:19]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[NH:14][C:15]([O:17][CH3:18])=[O:16].[N+:52]([C:55]1[CH:60]=[CH:59][C:58]([S:61](Cl)(=[O:63])=[O:62])=[CH:57][CH:56]=1)([O-:54])=[O:53].S(Cl)(Cl)(=O)=O>N1C=CC=CC=1>[Si:35]([O:34][CH2:33][C@@H:2]([NH:1][S:61]([C:58]1[CH:57]=[CH:56][C:55]([N+:52]([O-:54])=[O:53])=[CH:60][CH:59]=1)(=[O:62])=[O:63])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12](=[O:32])[C@H:13]([CH:19]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[NH:14][C:15]([O:17][CH3:18])=[O:16])([C:48]([CH3:51])([CH3:50])[CH3:49])([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

5

Reactant 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 24648Sulfuryl chlorideHCID 68029330N-{2-[(3S)-3-amino-4-{[tert-butyl(diphenyl)silyl]oxy}butyl]phenyl}-Nalpha-(methoxycarbonyl)-beta-phenyl-L-phenylalaninamide

Product 1

HCID 86708031N-{2-[(3S)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-{[(4-nitrophenyl)sulfonyl]amino}butyl]phenyl}-Nalpha-(methoxycarbonyl)-beta-phenyl-L-phenylalaninamideYield 101.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of N-{2-[(3S)-3-amino-4-{[tert-butyl(diphenyl)silyl]oxy}butyl]phenyl}-Nα-(methoxycarbonyl)-β-phenyl-L-phenylalaninamide (8, 255.1 mg, 0.364 mmol) in pyridine (2 mL) was treated with solid p-nitro benzenesulfonyl chloride (247 mg, 1.115 mmol) (or any other suitable sulfonyl chloride) and the mixture stirred at room temperature for 13 h, quenched with sat. NaHCO3 (0.5 mL), diluted with DCM, washed with sat. NaHCO3 then aqueous 5% KHSO4 then saturated NaHCO3, dried over MgSO4, filtered and concentrated to get 326 mg (100% yield) of the title compound, which was used without further purification for the next step. MS: m/z=885.3 (MH+).

Workup

  1. customquenched with sat. NaHCO3 (0.5 mL)
  2. additiondiluted with DCM
  3. washwashed with sat. NaHCO3
  4. dry with materialaqueous 5% KHSO4 then saturated NaHCO3, dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-183eece9483d48bb9170456eed671bd5
Source dataset
uspto-grants-2015_11
Patent number
US09187415B2

Reaction notes

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