Methanol → HCID 86639016, compound

HRID 1662300Notes

Reaction equation

HRID 1662300 reaction equation
C([O:8][C@@H:9]1[C@H:13]([O:14]CC2C=CC=CC=2)[C@@H:12]([CH2:22][O:23]CC2C=CC=CC=2)[O:11][CH:10]1[N:31]1[CH:35]=[C:34]([I:36])[CH:33]=[C:32]1[CH:37]=[O:38])C1C=CC=CC=1.CO.[NH4+].[OH-].O>ClCCl.B(Br)(Br)Br>[C@@H:10]1([N:31]2[CH:35]=[C:34]([I:36])[CH:33]=[C:32]2[CH:37]=[O:38])[O:11][C@H:12]([CH2:22][OH:23])[C@@H:13]([OH:14])[C@H:9]1[OH:8]

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14923Ammonium HydroxideHCID 86639017HCID 86639017, compound

Product 1

HCID 86639016HCID 86639016, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 25134Boron tribromideSolvent

Procedure

To 1-(2,3,5-tri-O-benzyl-D-ribofuranosyl)-4-iodopyrrole-2-carbaldehyde in dichloromethane (15 ml), BBr3 (1 M, 8.5 ml) was added at −78° C. The reaction mixture was stirred for 2 hours, followed by addition of 50% methanol in CH2Cl2 (30 ml). After this solution was stirred at −78° C. for 10 minutes, 28% NH4OH (4 ml) was added and the reaction mixture was stirred until it reached room temperature. The solution was added to CH2Cl2 and H2O. The aqueous layer was partitioned and washed three times with CH2Cl2, and the residue was concentrated under reduced pressure. The product was purified by reversed-phase C18 HPLC to give 1-(β-D-ribofuranosyl)-4-iodopyrrole-2-carbaldehyde (330 mg).

Workup

  1. stirringAfter this solution was stirred at −78° C. for 10 minutes
  2. stirringthe reaction mixture was stirred until it
  3. customreached room temperature
  4. customThe aqueous layer was partitioned
  5. washwashed three times with CH2Cl2
  6. concentrationthe residue was concentrated under reduced pressure
  7. customThe product was purified by reversed-phase C18 HPLC

Sources & evidence

ORD record
ord-198a36f69e4e4382b16b63b8416c201f
Source dataset
uspto-grants-2011_10
Patent number
US08030478B2

Reaction notes

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