Thiophenol → Methyl 3-[2-(2,6-bis-hydroxymethyl-pyridin-4-yloxy)-ethylamino]-propanoate

HRID 2173757Notes

Reaction equation

HRID 2173757 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][CH2:11][N:12](S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:6]=[C:5]([CH2:31][OH:32])[N:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(S)C=CC=CC=1>C(#N)C>[OH:32][CH2:31][C:5]1[CH:6]=[C:7]([O:9][CH2:10][CH2:11][NH:12][CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:8]=[C:3]([CH2:2][OH:1])[N:4]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 10796Cesium carbonateHCID 66714015Methyl 3-[[2-(2,6-bis-hydroxymethyl-pyridin-4-yloxy)-ethyl]-(2-nitro-benzenesulfonyl)-amino]-propanoate

Product 1

HCID 66714165Methyl 3-[2-(2,6-bis-hydroxymethyl-pyridin-4-yloxy)-ethylamino]-propanoateYield 87.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 155 mg of methyl 3-[[2-(2,6-bis-hydroxymethyl-pyridin-4-yloxy)-ethyl]-(2-nitro-benzenesulfonyl)-amino]-propanoate in 6 ml of acetonitrile, under argon, was added 325 mg of caesium carbonate and 67 μl of thiophenol. The mixture was stirred for 4 hours at room temperature and then filtered through a sinter of porosity 4. The cake was washed with EtOAc and the filtrate was concentrated under reduced pressure and purified on a Mega BE-SCX, 2GM 12ML cartridge (Varian), using washing with MeOH and detachment of the expected product with a 2N solution of ammonia in MeOH. The fractions containing the desired product were combined and concentrated under reduced pressure. 82 mg of methyl 3-[2-(2,6-bis-hydroxymethyl-pyridin-4-yloxy)-ethylamino]-propanoate were obtained. LC/MS (B): tr=0.33 min; [M+H]+: m/z 285.

Workup

  1. filtrationfiltered through a sinter of porosity 4
  2. washThe cake was washed with EtOAc
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. custompurified on a Mega BE-SCX, 2GM 12ML cartridge (Varian)
  5. washusing washing with MeOH and detachment of the expected product with a 2N solution of ammonia in MeOH
  6. additionThe fractions containing the desired product
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-10928100104444e49831e5c6255eca2c
Source dataset
uspto-grants-2015_06
Patent number
US09056914B2

Reaction notes

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