Methanol → HCID 67246087, compound

HRID 885548Notes

Reaction equation

HRID 885548 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][C:17]([C:20]1[CH:21]=[C:22]([NH2:26])[CH:23]=[CH:24][CH:25]=1)([F:19])[F:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:27]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[C:28]=[O:29].CO>C(Cl)Cl>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][C:17]([C:20]1[CH:21]=[C:22]([NH:26][C:28]([NH:27][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:29])[CH:23]=[CH:24][CH:25]=1)([F:19])[F:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 76283Ethyl isocyanatoacetateHCID 67246243HCID 67246243, compound

Product 1

HCID 67246087HCID 67246087, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Intermediate 58 (3.9 g, 10.7 mmol) in methylene chloride (35 mL) was added ethyl isocyanatoacetate (1.38 mL, 12.3 mmol). The mixture was stirred at room temperature for 5 hours. The crude reaction was cooled to 0° C. and then methanol (2.3 mL) was added. The mixture was stirred at room temperature for 0.5 hours and the solvent was removed under reduced pressure. Purification by column chromatography using methylene chloride/methanol (from pure methylene chloride to 98:2) as eluent gave the title compound (5.1 g, 95%) as oil.

Workup

  1. customThe crude reaction
  2. temperaturewas cooled to 0° C.
  3. stirringThe mixture was stirred at room temperature for 0.5 hours
  4. customthe solvent was removed under reduced pressure
  5. customPurification by column chromatography

Sources & evidence

ORD record
ord-fd5ad2f0b2724490a5bb0f7169a2093a
Source dataset
uspto-grants-2012_08
Patent number
US08242177B2

Reaction notes

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