Benzylamine → N-[5-((1R)-2-Benzylamino-1-triethylsilanyloxy-ethyl)-2-benzyloxy-phenyl]-methanesulfonamide

HRID 479949Notes

Reaction equation

HRID 479949 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:18][Si:19]([CH2:24][CH3:25])([CH2:22][CH3:23])[CH2:20][CH3:21])[CH2:16]I)=[CH:11][C:10]=1[NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:31]([NH2:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>>[CH2:31]([NH:38][CH2:16][C@@H:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:10]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH:11]=1)[O:18][Si:19]([CH2:24][CH3:25])([CH2:22][CH3:23])[CH2:20][CH3:21])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 54211801(R)-N-[2-benzyloxy-5-(2-iodo-1-triethylsilyloxyethyl)phenyl]methanesulfonamide

Product 1

HCID 69952868N-[5-((1R)-2-Benzylamino-1-triethylsilanyloxy-ethyl)-2-benzyloxy-phenyl]-methanesulfonamideYield 81.4%

Conditions

Temperature
65 °C

Procedure

N-[2-benzyloxy-5-((1R)-2-iodo-1-triethylsilanyloxy-ethyl)-phenyl]-methanesulfonamide (0.56 g, 1 mmol) was dissolved in benzylamine (0.54 g, 5 mmol) and stirred at 65° C. for 22 h. The mixture was then cooled to room temperature, and stirred with hexanes. The hexanes solution was filtered through a pad of silica gel, and the residue was stirred with ether (10 ml). The ether solution was diluted with 10 ml of hexanes, and passed through the silica gel pad. The filter pad was eluted with ether-hexanes (1:1 to 3:1), and the filtrate was evaporated. The residue was washed with isooctane to give 0.44 g of a colorless gum; MS (ES) m/z 541.1 (MH+); HRMS (EI) Calcd. for C29H40N2O4SSi (M+): 540.2478, Found: 540.2472.

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. filtrationThe hexanes solution was filtered through a pad of silica gel
  3. stirringthe residue was stirred with ether (10 ml)
  4. additionThe ether solution was diluted with 10 ml of hexanes
  5. washThe filter pad was eluted with ether-hexanes (1:1 to 3:1)
  6. customthe filtrate was evaporated
  7. washThe residue was washed with isooctane

Sources & evidence

ORD record
ord-c70cf55c1e294d00a0056770588e39fd
Source dataset
uspto-grants-2003_11
Patent number
US06649603B2

Reaction notes

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