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

HRID 1158257Notes

Reaction equation

HRID 1158257 reaction equation
[O:1]1[CH:5]2[O:6][CH2:7][CH2:8][CH:4]2[CH:3]([O:9][C:10](=[O:28])[NH:11][CH:12]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:13]([OH:20])[CH2:14][NH:15][CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:2]1.C(=O)(O)[O-].[Na+].[O:34]=[C:35]1[CH2:43][C:42]2[C:37](=[CH:38][CH:39]=[C:40]([S:44](Cl)(=[O:46])=[O:45])[CH:41]=2)[NH:36]1>C(Cl)Cl.C(OCC)(=O)C>[O:1]1[CH:5]2[O:6][CH2:7][CH2:8][CH:4]2[CH:3]([O:9][C:10](=[O:28])[NH:11][CH:12]([CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:13]([OH:20])[CH2:14][N:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[S:44]([C:40]2[CH:41]=[C:42]3[C:37](=[CH:38][CH:39]=2)[NH:36][C:35](=[O:34])[CH2:43]3)(=[O:45])=[O:46])[CH2:2]1

Participants

6

Reactant 3

HCID 516892Sodium Bicarbonate2×HCID 49625062-oxo-2,3-dihydro-1H-indole-5-sulfonyl chlorideHCID 21055240(1-Benzyl-2-hydroxy-3-isobutylamino-propyl)-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester

Product 1

HCID 58612411{1-Benzyl-2-hydroxy-3-[isobutyl-(2-oxo-2,3-dihydro-1H-indole-5-sulfonyl)-amino]-propyl}-carbamic acid hexahydro-furo[2,3-b]furan-3-yl esterYield 90%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1-benzyl-2-hydroxy-3-isobutylamino-propyl)-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester 19 (59 mg, 0.15 mmol) in CH2Cl2 (1.6 ml) was added saturated aqueous sodium bicarbonate (0.4 ml), solid sodium bicarbonate (16 mg, 0.19 mmol), and then 2-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride 14 (42 mg, 0.18 mmol). The mixture was stirred overnight, diluted with ethyl acetate, washed with saturated brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to provide the title product as a white solid, (79 mg, 90%). TLC: Rf 0.33 (Ethyl acetate). MS m/z 588 (MH)+. 1H NMR (CDCl3) is consistent with the structure.

Workup

  1. washwashed with saturated brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9f74c7cdf5a34a7086ebad7cc362527b
Source dataset
uspto-grants-2010_10
Patent number
US07807845B2

Reaction notes

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