Acetic Acid → [(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[3-[(4-bromophenyl)methyl]-4-methyl-indolin-1-yl]tetrahydropyran-2-yl]methyl acetate

HRID 2284525Notes

Reaction equation

HRID 2284525 reaction equation
[C:1]([O:4][CH2:5][C@@H:6]1[CH:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:9]([O:20][C:21](=[O:23])[CH3:22])[C@H:8](OC(=O)C)[O:7]1)(=[O:3])[CH3:2].[Br:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][CH:36]2[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][C:43]=3[CH3:45])[NH:38][CH2:37]2)=[CH:31][CH:30]=1.C(O)(=O)C>CO>[C:1]([O:4][CH2:5][C@@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:9]([O:20][C:21](=[O:23])[CH3:22])[C@H:8]([N:38]2[C:39]3[C:44](=[C:43]([CH3:45])[CH:42]=[CH:41][CH:40]=3)[CH:36]([CH2:35][C:32]3[CH:31]=[CH:30][C:29]([Br:28])=[CH:34][CH:33]=3)[CH2:37]2)[O:7]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1180213123-[(4-Bromophenyl)methyl]-4-methyl-indolineHCID 118021333[(2R,4S,5R,6S)-3,4,5,6-tetraacetoxytetrahydropyran-2-yl]methyl acetate

Product 1

HCID 118021460[(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-[3-[(4-bromophenyl)methyl]-4-methyl-indolin-1-yl]tetrahydropyran-2-yl]methyl acetateYield 34%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add [(2R,4S,5R,6S)-3,4,5,6-tetraacetoxytetrahydropyran-2-yl]methyl acetate (10.6 mmol) and 3-[(4-bromophenyl)methyl]-4-methyl-indoline (10.6 mmol) to a solution of acetic acid (69.8 mmol) in methanol (80 mL). Stir at room temperature overnight. Filter the reaction mixture through a glass frit and wash the filter cake with methanol (2×10 mL). Dry the filter cake under vacuum to yield the title compound (2.3g, 3.6 mmol): MS (m/z): 632 (M+H).

Workup

  1. filtrationFilter the reaction mixture through a glass frit
  2. washwash the filter cake with methanol (2×10 mL)
  3. customDry the filter cake under vacuum

Sources & evidence

ORD record
ord-997de43c89c74f758b071363fdcc4b44
Source dataset
uspto-grants-2015_09
Patent number
US09145435B2

Reaction notes

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