2-[(Methylsulfonyl)amino]benzimidazol-5-ylsulfonyl chloride → tert-Butyl-N-((1S,2R)-1-benzyl-3-(isopropyloxy) (2-[(methylsulfonyl)amino]benzimidazol-5-ylsulfonyl)amino-2-hydroxypropyl)carbamate

HRID 29149Notes

Reaction equation

HRID 29149 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C@@H:8]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C@H:9]([OH:16])[CH2:10][NH:11]OC(C)C)([CH3:4])([CH3:3])[CH3:2].[CH3:25][S:26]([NH:29][C:30]1[NH:31][C:32]2[CH:38]=[C:37]([S:39](Cl)(=[O:41])=[O:40])[CH:36]=[CH:35][C:33]=2[N:34]=1)(=[O:28])=[O:27]>N1C=CC=CC=1>[C:1]([O:5][C:6](=[O:24])[NH:7][C@@H:8]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C@@H:9]([OH:16])[CH:10]([NH:11][S:39]([C:37]1[CH:36]=[CH:35][C:33]2[N:34]=[C:30]([NH:29][S:26]([CH3:25])(=[O:28])=[O:27])[NH:31][C:32]=2[CH:38]=1)(=[O:41])=[O:40])[O:5][CH:1]([CH3:3])[CH3:2])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 229970162-[(Methylsulfonyl)amino]benzimidazol-5-ylsulfonyl chlorideHCID 86592444tert-Butyl-N-((1S,2R)-1-benzyl-3-(isopropyloxy)amino-2-hydroxypropyl)carbamate

Product 1

HCID 86592443tert-Butyl-N-((1S,2R)-1-benzyl-3-(isopropyloxy) (2-[(methylsulfonyl)amino]benzimidazol-5-ylsulfonyl)amino-2-hydroxypropyl)carbamate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

tert-Butyl-N-((1S,2R)-1-benzyl-3-(isopropyloxy)amino-2-hydroxypropyl)carbamate (86 mg, 0.25 mmol) was combined with 2-[(methylsulfonyl)amino]benzimidazol-5-ylsulfonyl chloride (77 mg, 0.25 mmol) in anhydrous pyridine (1 ml) with a catalytic amount of N,N-dimethylaminopyridine. The reaction was stirred at room temperature overnight. The solvent was evaporated under vacuum. The crude mixture was diluted in EtOAc and washed with water and brine. Organic phase was dried with MgSO4 and solvent was removed in vacuo. Purification by TLC prep (2% MeOH/CH2Cl2). Recovered 56 mg (37%) of product as a white solid. HPLC showed the material to be 98% pure; Ret. time=9.87 min. 1H NMR (CDCl3): 7.12-8.04 (m, 8H), 6.5 (m, 1H), 4.47-4.51 (m, 2H), 3.68 (m, 2H), 3.22 (s, 3H), 2.81-2.88 (m, 3H), 1.75 (m, 2H), 1.22 (s, 9H), 1.16 (d, 6H). MS (ES+): obs. M+H@ 612.1 amu.

Workup

  1. customThe solvent was evaporated under vacuum
  2. additionThe crude mixture was diluted in EtOAc
  3. washwashed with water and brine
  4. dry with materialOrganic phase was dried with MgSO4 and solvent
  5. customwas removed in vacuo
  6. customPurification by TLC prep (2% MeOH/CH2Cl2)
  7. customRecovered 56 mg (37%) of product as a white solid

Sources & evidence

ORD record
ord-95ae70552ab2460aa2741b521fa33488
Source dataset
uspto-grants-2008_09
Patent number
US07419967B2

Reaction notes

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