2-Amino-2-methyl-1-propanol → (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-5-[4-[(1E)-4-[(2-hydroxy-1,1-dimethylethyl)amino]-4-oxobut-1-en-1-yl]benzyl]-4-methylphenyl]-D-glucitol

HRID 1009881Notes

Reaction equation

HRID 1009881 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C@H:10]1[C:40]1[CH:45]=[C:44]([CH2:46][C:47]2[CH:52]=[CH:51][C:50](/[CH:53]=[CH:54]/[CH2:55][C:56](O)=[O:57])=[CH:49][CH:48]=2)[C:43]([CH3:59])=[CH:42][C:41]=1[O:60][CH2:61][C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:68][C:69]([CH3:73])([CH3:72])[CH2:70][OH:71].ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C>O.C(Cl)(Cl)Cl>[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C@H:10]1[C:40]1[CH:45]=[C:44]([CH2:46][C:47]2[CH:48]=[CH:49][C:50](/[CH:53]=[CH:54]/[CH2:55][C:56]([NH:68][C:69]([CH3:73])([CH3:72])[CH2:70][OH:71])=[O:57])=[CH:51][CH:52]=2)[C:43]([CH3:59])=[CH:42][C:41]=1[O:60][CH2:61][C:62]1[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 118072-Amino-2-methyl-1-propanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 67303958(1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-5-[4-[(1E)-3-carboxyprop-1-en-1-yl]benzyl]-4-methylphenyl]-D-glucitol

Product 1

HCID 86638444(1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-5-[4-[(1E)-4-[(2-hydroxy-1,1-dimethylethyl)amino]-4-oxobut-1-en-1-yl]benzyl]-4-methylphenyl]-D-glucitolYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a chloroform solution (2.2 mL) of (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-5-[4-[(1E)-3-carboxyprop-1-en-1-yl]benzyl]-4-methylphenyl]-D-glucitol (200 mg, 0.223 mmol) were added 2-amino-2-methyl-1-propanol (40 mg, 0.446 mmol), 1-hydroxy benzotriazole (33 mg, 0.245 mmol) and WSC (60 mg, 0.312 mmol), and the mixture was stirred overnight at room temperature. To the reaction solution was added water, and the resulting mixture was extracted with chloroform. The organic layer was washed with brine, and dried with anhydrous magnesium sulfate. The drying agent was filtered off, and the solvent was evaporated under reduced pressure. Thus obtained residue was purified with silica gel column chromatography (hexane:ethyl acetate=5:1 to 1:2) to obtain the title compound (120 mg, 56%) as an orange-yellow oily compound.

Workup

  1. extractionthe resulting mixture was extracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried with anhydrous magnesium sulfate
  4. filtrationThe drying agent was filtered off
  5. customthe solvent was evaporated under reduced pressure
  6. customThus obtained residue was purified with silica gel column chromatography (hexane:ethyl acetate=5:1 to 1:2)

Sources & evidence

ORD record
ord-4243538422b54025a0cc4bc0e2f30d33
Source dataset
uspto-grants-2011_07
Patent number
US07973012B2

Reaction notes

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