2,4-Difluorobenzylamine → (1-Benzyl-3-{[3-(2,4-difluoro-benzylamino)-4-nitro-benzenesulfonyl]-isobutyl-amino}-2-hydroxy-propyl)-carbamic Acid hexahydro-furo[2,3-b]furan-3-yl Ester

HRID 660426Notes

Reaction equation

HRID 660426 reaction equation
[O:1]1[CH:5]2[O:6][CH2:7][CH2:8][CH:4]2[CH:3]([O:9][C:10](=[O:41])[NH:11][CH:12]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:13]([OH:33])[CH2:14][N:15]([S:20]([C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[C:25](F)[CH:24]=2)(=[O:22])=[O:21])[CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:2]1.[F:42][C:43]1[CH:50]=[C:49]([F:51])[CH:48]=[CH:47][C:44]=1[CH2:45][NH2:46]>O1CCCC1>[O:1]1[CH:5]2[O:6][CH2:7][CH2:8][CH:4]2[CH:3]([O:9][C:10](=[O:41])[NH:11][CH:12]([CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:13]([OH:33])[CH2:14][N:15]([S:20]([C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[C:25]([NH:46][CH2:45][C:44]3[CH:47]=[CH:48][C:49]([F:51])=[CH:50][C:43]=3[F:42])[CH:24]=2)(=[O:22])=[O:21])[CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:2]1

Participants

4

Reactant 2

HCID 27332442,4-DifluorobenzylamineHCID 68508884{1-Benzyl-3-[(3-fluoro-4-nitro-benzenesulfonyl)-isobutyl-amino]-2-hydroxy-propyl}-carbamic Acid hexahydro-furo[2,3-b]furan-3-yl Ester

Product 1

HCID 69155346(1-Benzyl-3-{[3-(2,4-difluoro-benzylamino)-4-nitro-benzenesulfonyl]-isobutyl-amino}-2-hydroxy-propyl)-carbamic Acid hexahydro-furo[2,3-b]furan-3-yl EsterYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

{1-Benzyl-3-[(3-fluoro-4-nitro-benzenesulfonyl)-isobutyl-amino]-2-hydroxy-propyl}-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester (7) (0.40 g, 0.67 mmol, 1 equiv) and 2,4-difluoro-benzylamine (0.14 g, 1 mmol, 1.49 equiv) were dissolved in tetrahydrofurane (10 mL). The solution was heated to reflux for 18 h. The solution was concentrated and the crude product was dissolved in dichloromethane (15 mL). The organic layer was washed with saturated NaHCO3 solution (15 mL). The organic layer was separated and evaporated under reduced pressure to yield the title compound (0.48 g, 0.67 mmol, quantitative). LRMS (ES+): m/z 719 [M+H]+.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 18 h
  3. concentrationThe solution was concentrated
  4. dissolutionthe crude product was dissolved in dichloromethane (15 mL)
  5. washThe organic layer was washed with saturated NaHCO3 solution (15 mL)
  6. customThe organic layer was separated
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-47dafd42dc0b4ea084f174b980f37af4
Source dataset
uspto-grants-2011_12
Patent number
US08084494B2

Reaction notes

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