Methylamine → HCID 68905785, compound

HRID 2110347Notes

Reaction equation

HRID 2110347 reaction equation
[OH:1][CH:2]([CH:7]([N:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17]1)[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[C:3](OC)=[O:4].[CH3:25][NH2:26]>>[OH:1][CH:2]([CH:7]([N:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17]1)[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[C:3]([NH:26][CH3:25])=[O:4]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 86600897HCID 86600897, compound

Product 1

HCID 68905785HCID 68905785, compoundYield 80%

Procedure

A solution of methyl (2SR,3SR)-2-hydroxy-3-(1H-indol-1-yl)-3-(4-methoxyphenyl)propanoate (2.43 g, 7.5 mmol) in methylamine solution (33% wt. in absolute ethanol, 40 mL) was heated to 75° C. in a sealed tube for 1 hour . The cooled reaction mixture was then concentrated under reduced pressure to afford a yellow syrup. Purification by crystallization from 80% chloroform/hexane (50 mL) afforded 1.93 g (80%) of (2SR,3SR)-2-hydroxy-3-(1H-indol-1-yl)-3-(4-methoxyphenyl)-N-methylpropanamide as a white crystalline solid. MS (ES) m/z 323.2 ([M−H]−); HRMS: calcd for C19H20N2O3+H+, 325.15467; found (ESI, [M+H]+), 325.1562.

Workup

  1. customThe cooled reaction mixture
  2. concentrationwas then concentrated under reduced pressure
  3. customto afford a yellow syrup
  4. customPurification
  5. customby crystallization from 80% chloroform/hexane (50 mL)

Sources & evidence

ORD record
ord-2edce2641c424ccda552e1877a593554
Source dataset
uspto-grants-2009_04
Patent number
US07517899B2

Reaction notes

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