Sodium Bicarbonate → {3-[(Benzofuran-5-sulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester

HRID 2224670Notes

Reaction equation

HRID 2224670 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([S:10](Cl)(=[O:12])=[O:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1.[O:14]1[CH:18]2[O:19][CH2:20][CH2:21][CH:17]2[CH:16]([O:22][C:23](=[O:41])[NH:24][CH:25]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:26]([OH:33])[CH2:27][NH:28][CH2:29][CH:30]([CH3:32])[CH3:31])[CH2:15]1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[O:14]1[CH:18]2[O:19][CH2:20][CH2:21][CH:17]2[CH:16]([O:22][C:23](=[O:41])[NH:24][CH:25]([CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:26]([OH:33])[CH2:27][N:28]([S:10]([C:8]2[CH:7]=[CH:6][C:5]3[O:1][CH:2]=[CH:3][C:4]=3[CH:9]=2)(=[O:12])=[O:11])[CH2:29][CH:30]([CH3:32])[CH3:31])[CH2:15]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21055240(1-Benzyl-2-hydroxy-3-isobutylamino-propyl)-carbamic acid hexahydro-furo[2,3-b]furan-3-yl esterHCID 53403186Benzofuran-5-sulfonyl chloride

Product 1

HCID 66769907{3-[(Benzofuran-5-sulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzofuran-5-sulfonyl chloride 148 mg (0.68 mmol) was dissolved in 5 mL of methylene chloride. (1-Benzyl-2-hydroxy-3-isobutylamino-propyl)-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester 19 (244 mg, 0.62 mmol) was added followed by 0.63 mL 10% NaHCO3 solution (0.75 mmol). The reaction was stirred at room temperature for 16 hours. The organic phase was separated and loaded onto silica gel in methylene chloride. The excess of benzofuran-5-sulfonyl chloride was washed out by several portions of methylene chloride. The final product was obtained by eluting with 3/1 ethyl acetate/methylene chloride. Concentration in vacuo afforded 350 mg (98.5% yield) of the final product with HPLC purity of >97% (220 nm). The product can be recrystallized from ethyl acetate/hexanes to get colorless crystals m.p. 122-124° C. MS 573 (MH)+.

Workup

  1. customThe organic phase was separated
  2. washThe excess of benzofuran-5-sulfonyl chloride was washed out by several portions of methylene chloride

Sources & evidence

ORD record
ord-9ab5b61a78ba4f0aa412002431a7f5c7
Source dataset
uspto-grants-2008_05
Patent number
US07378441B2

Reaction notes

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