Methanol → HCID 89622329, compound

HRID 1500817Notes

Reaction equation

HRID 1500817 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:21]3[S:22][C:23]4[C:29]([O:30][CH3:31])=[CH:28][C:27]([CH3:32])=[CH:26][C:24]=4[CH:25]=3)[C:9]([CH2:13][N:14]3[CH2:19][CH2:18][NH:17][C:16](=[O:20])[CH2:15]3)=[C:10]([CH2:11][OH:12])[N:6]2[N:5]=[CH:4][N:3]=1.S(Cl)(Cl)=O.[CH3:37]O.C[O-].[Na+]>ClCCl>[NH2:1][C:2]1[C:7]2=[C:8]([C:21]3[S:22][C:23]4[C:29]([O:30][CH3:31])=[CH:28][C:27]([CH3:32])=[CH:26][C:24]=4[CH:25]=3)[C:9]([CH2:13][N:14]3[CH2:19][CH2:18][NH:17][C:16](=[O:20])[CH2:15]3)=[C:10]([CH2:11][O:12][CH3:37])[N:6]2[N:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 887Methanol2×HCID 24386Thionyl Chloride2×HCID 10942334Sodium MethoxideHCID 89622338HCID 89622338, compound

Product 1

HCID 89622329HCID 89622329, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of Example 125 (88 mg, 194 μmol) in dichloromethane (5 ml) was treated with thionyl chloride (29 μl, 389 μmol), and the mixture was stirred at rt for 65 min. Another portion of thionyl chloride (29 μl, 389 μmol) was added, and stirring was continued for 1.5 h. An excess of methanol was then added, followed by dropwise addition of a 5.4 M solution of sodium methylate in methanol (84 mg, 1.56 mmol) until pH 8 was reached. After stirring for 3 days, the volatiles were evaporated under reduced pressure, and the residue was separated by preparative RP-HPLC (Reprosil C18, gradient 20-40% acetonitrile/0.2% aq. trifluoroacetic acid). The product fractions were evaporated to yield 19 mg of the title compound (21% of th.).

Workup

  1. stirringstirring
  2. waitwas continued for 1.5 h
  3. stirringAfter stirring for 3 days
  4. customthe volatiles were evaporated under reduced pressure
  5. customthe residue was separated by preparative RP-HPLC (Reprosil C18, gradient 20-40% acetonitrile/0.2% aq. trifluoroacetic acid)
  6. customThe product fractions were evaporated

Sources & evidence

ORD record
ord-55b823fbde73400ca0ce9c694ea8326a
Source dataset
uspto-grants-2015_12
Patent number
US09206184B2

Reaction notes

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