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

HRID 1158258Notes

Reaction equation

HRID 1158258 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]([CH2:29][CH:30]([CH3:32])[CH3:31])[S:16]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[NH:24][C:23](=[O:28])[CH2:22]3)(=[O:18])=[O:17])[CH2:2]1.CO[CH:44](OC)[N:45]([CH3:47])[CH3:46]>C(Cl)(Cl)Cl>[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:16]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[NH:24][C:23](=[O:28])[C:22]3=[CH:44][N:45]([CH3:47])[CH3:46])(=[O:18])=[O:17])[CH2:29][CH:30]([CH3:31])[CH3:32])[CH2:2]1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 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 ester

Product 1

HCID 67371409{1-Benzyl-3-[(3-dimethylaminomethylene-2-oxo-2,3-dihydro-1H-indole-5-sulfonyl)-isobutyl-amino]-2-hydroxy-propyl}-carbamic acid hexahydro-furo[2,3-b]furan-3-yl esterYield 75%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of {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 20 (59 mg, 0.1 mmol) and N,N-dimethylformamide dimethylacetal (27 ul, 0.2 mmol) in 1 ml of chloroform was refluxed for 1 h, cooled, and concentrated in vacuo. The residue was chromatographed on silica gel, (methanol:ethyl acetate 3:97) to obtain {1-benzyl-3-[(3-dimethylaminomethylene-2-oxo-2,3-dihydro-1H-indole-5-sulfonyl)-isobutyl-amino]-2-hydroxy-propyl}-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester 21 (48 mg, 75%). TLC: Rf 0.09 (ethyl acetate). MS m/z 643 (MH)+. 1H NMR (CDCl3) consistent with structure.

Workup

  1. temperaturecooled
  2. concentrationconcentrated in vacuo
  3. customThe residue was chromatographed on silica gel, (methanol:ethyl acetate 3:97)

Sources & evidence

ORD record
ord-aee6451ab39744078abe202019be3e0e
Source dataset
uspto-grants-2010_10
Patent number
US07807845B2

Reaction notes

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