Tetrahydrofuran → HCID 86755946, compound

HRID 367348Notes

Reaction equation

HRID 367348 reaction equation
[OH:1][CH:2]([C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([CH2:29][OH:30])[CH:23]=1)[CH2:3][NH:4][C@H:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][C:17]([O:19]CC)=[O:18])=[CH:10][CH:11]=2)[CH2:6]1.[O:31]1CC[CH2:33][CH2:32]1>CNC>[OH:1][CH:2]([C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([CH2:29][OH:30])[CH:23]=1)[CH2:3][NH:4][C@H:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][C:17]([O-:19])=[O:18])=[CH:10][CH:11]=2)[CH2:6]1.[CH3:3][N:4]([CH3:5])[C:32](=[O:31])[CH3:33]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 54304925HCID 54304925, compound

Product 1

HCID 86755946HCID 86755946, compound

Reagents, catalysts & solvents 1

HCID 674DimethylamineSolvent

Procedure

Ethyl 2-[(2S)-2-[[(2RS)-2-hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl)ethyl]amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]acetate (2.00 g) was dissolved in a solution of 17.9 g of dimethylamine in 10 ml of tetrahydrofuran, and the solution was sealed in a tube and subjected to 36 hours of reaction at 65° C. The reaction solution was concentrated under reduced pressure and the resulting residue was purified by aminopropylated silica gel medium pressure liquid column chromatography (eluent: chloroform/methanol=10/1) to give 1.58 g of amorphous 2-[(2S)-2-[[(2RS)-2-hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl)ethyl]amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]acetate-N,N-dimethylacetamide (Compound 1).

Workup

  1. customthe solution was sealed in a tube
  2. customsubjected to 36 hours of reaction at 65° C
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. customthe resulting residue was purified by aminopropylated silica gel medium pressure liquid column chromatography (eluent: chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-c1931aa2f703405b9855661965cf015c
Source dataset
uspto-grants-2000_10
Patent number
US06133266

Reaction notes

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