Ethanol → HCID 117830973, compound

HRID 515930Notes

Reaction equation

HRID 515930 reaction equation
[F:1][C:2]1[C:3]([O:53]C)=[CH:4][C:5]([C:34]([N:36]2[C@H:45]([CH2:46][N:47]3[CH2:52][CH2:51][O:50][CH2:49][CH2:48]3)[CH2:44][C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH2:37]2)=[O:35])=[C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH3:14])=[C:10]([C:15]([N:17]([C:24]3[CH:25]=[C:26]4[CH:32]=[CH:31][N:30]([CH3:33])[C:27]4=[N:28][CH:29]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:16])[CH:9]=2)[CH:7]=1.B(Br)(Br)Br.C(O)C.C(=O)(O)[O-].[Na+]>ClCCl>[F:1][C:2]1[C:3]([OH:53])=[CH:4][C:5]([C:34]([N:36]2[C@H:45]([CH2:46][N:47]3[CH2:48][CH2:49][O:50][CH2:51][CH2:52]3)[CH2:44][C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH2:37]2)=[O:35])=[C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH3:14])=[C:10]([C:15]([N:17]([C:24]3[CH:25]=[C:26]4[CH:32]=[CH:31][N:30]([CH3:33])[C:27]4=[N:28][CH:29]=3)[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:16])[CH:9]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 117830994HCID 117830994, compound

Product 1

HCID 117830973HCID 117830973, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the compound of Step A (1 g; 1.37 mmol) in anhydrous dichloromethane (10 mL) there is added, dropwise at 0° C., a 1M solution of boron tribromide in dichloromethane (1.8 mL; 1.8 mmol). After stirring for 15 hours at ambient temperature, the reaction mixture is poured dropwise into a solution of ethanol (15 mL) at −10° C. After stirring for one hour, saturated aqueous sodium bicarbonate solution is added, and the reaction mixture is extracted with dichloromethane. After drying over MgSO4, the residue is purified on a silica gel column using a mixture of dichloromethane and methanol as eluant to yield the expected product.

Workup

  1. stirringAfter stirring for one hour
  2. extractionthe reaction mixture is extracted with dichloromethane
  3. dry with materialAfter drying over MgSO4
  4. customthe residue is purified on a silica gel column
  5. additiona mixture of dichloromethane and methanol as eluant

Sources & evidence

ORD record
ord-f87753190c45442480abc3a42161be46
Source dataset
uspto-grants-2015_08
Patent number
US09108983B2

Reaction notes

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