Methanol → HCID 136342633, compound

HRID 418707Notes

Reaction equation

HRID 418707 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:11]2[S:19][C:18]3[C:13](=[N:14][CH:15]=[CH:16][C:17]=3[O:20][C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][C:22]=3[F:30])[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9]C.B(Br)(Br)Br.CO.[OH-].[Na+]>ClCCl>[F:30][C:22]1[CH:23]=[C:24]([N+:27]([O-:29])=[O:28])[CH:25]=[CH:26][C:21]=1[O:20][C:17]1[CH:16]=[CH:15][N:14]=[C:13]2[CH:12]=[C:11]([C:5]3[CH:4]=[C:3]([OH:2])[C:8]([OH:9])=[CH:7][CH:6]=3)[S:19][C:18]=12

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 66649265HCID 66649265, compound

Product 1

HCID 136342633HCID 136342633, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 331 (172 mg, 0.40 mmol) in anhydrous dichloromethane (20 ml) at −78° C. was slowly added BBr3 (˜4 mL, 1.0 M in CH2Cl2). The temperature was allowed to warm to room temperature over 1.5 hrs, and the reaction mixture was stirred overnight. After cooling to 0° C., MeOH and 1 N NaOH (few mL) were added, respectively. The reaction mixture was stirred for 1 h, concentrated, diluted with MeOH and water, shaken for 30 min, isolated by filtration, and rinsed with MeOH. The mother liquid was concentrated, dissolved in a minimum of MeOH, and diluted with a small amount of water. The pH of the solution was adjusted to 4 with 1N NaOH in order to get a pale brown suspension. After shaking for 15 min, the suspension was filtered off, rinsed with water, air-dried, and dried under high vacuum to afford the title compound 332 (154 mg, 96% yield) as a yellow-green solid. MS (m/z): 399.0 (M+H)+.

Workup

  1. customat −78° C.
  2. temperatureAfter cooling to 0° C.
  3. stirringThe reaction mixture was stirred for 1 h
  4. concentrationconcentrated
  5. additiondiluted with MeOH and water
  6. stirringshaken for 30 min
  7. customisolated by filtration
  8. washrinsed with MeOH
  9. concentrationThe mother liquid was concentrated
  10. dissolutiondissolved in a minimum of MeOH
  11. additiondiluted with a small amount of water
  12. customto get a pale brown suspension
  13. stirringAfter shaking for 15 min
  14. filtrationthe suspension was filtered off
  15. washrinsed with water
  16. customair-dried
  17. customdried under high vacuum

Sources & evidence

ORD record
ord-d36d115a575643dcbd261e7c0f13f289
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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