Tetrahydrofuran → (1S)-1-[5-[4-(2-aminoethoxy)-2-methylbenzyl]-2-(benzyloxy)-4-methylphenyl]-1,5-anhydro-2,3,4,6-tetra-O-benzyl-D-glucitol

HRID 1009876Notes

Reaction equation

HRID 1009876 reaction equation
O1CCCC1.[CH2:6]([O:13][C@@H:14]1[C@@H:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@H:18]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@@H:17]([CH2:36][O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[O:16][C@H:15]1[C:45]1[CH:50]=[C:49]([CH2:51][C:52]2[CH:57]=[CH:56][C:55]([O:58][CH2:59][CH2:60][N:61]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:54][C:53]=2[CH3:72])[C:48]([CH3:73])=[CH:47][C:46]=1[O:74][CH2:75][C:76]1[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.NN.[OH-].[Na+]>CO>[NH2:61][CH2:60][CH2:59][O:58][C:55]1[CH:56]=[CH:57][C:52]([CH2:51][C:49]2[C:48]([CH3:73])=[CH:47][C:46]([O:74][CH2:75][C:76]3[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=3)=[C:45]([C@@H:15]3[O:16][C@H:17]([CH2:36][O:37][CH2:38][C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[C@@H:18]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C@H:19]([O:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C@H:14]3[O:13][CH2:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:50]=2)=[C:53]([CH3:72])[CH:54]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 86638442HCID 86638442, compound

Product 1

HCID 67305276(1S)-1-[5-[4-(2-aminoethoxy)-2-methylbenzyl]-2-(benzyloxy)-4-methylphenyl]-1,5-anhydro-2,3,4,6-tetra-O-benzyl-D-glucitol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a tetrahydrofuran (0.8 mL) and methanol (0.2 mL) solution of (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-5-[4-[2-(1,3-dioxo-1,3-dihydro-2H-isoindole-2-yl)ethoxy]-2-methylbenzyl]-4-methylphenyl]-D-glucitol (60 mg, 0.059 mmol) was added hydrazine monohydrate (30 mg, 0.59 mmol), and the reaction mixture was stirred at 65° C. for an hour. After the mixture was cooled to room temperature, a 2 M aqueous solution of sodium hydroxide was added thereto, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain the title compound quantitatively.

Workup

  1. temperatureAfter the mixture was cooled to room temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4a38a38369e8410392990e62fc8375db
Source dataset
uspto-grants-2011_07
Patent number
US07973012B2

Reaction notes

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