Boron tribromide → HCID 54141791, compound

HRID 442795Notes

Reaction equation

HRID 442795 reaction equation
[NH2:1][C:2]([C:21]1[CH:26]=[CH:25][C:24]([C:27]([OH:29])=[O:28])=[C:23]([O:30]C)[CH:22]=1)([CH2:6][CH:7]1[C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:14][C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:3]([OH:5])=[O:4].B(Br)(Br)Br>ClCCl.O>[NH2:1][C:2]([C:21]1[CH:26]=[CH:25][C:24]([C:27]([OH:29])=[O:28])=[C:23]([OH:30])[CH:22]=1)([CH2:6][CH:7]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=2[O:14][C:15]2[C:20]1=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:3]([OH:5])=[O:4]

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 54087286HCID 54087286, compound

Product 1

HCID 54141791HCID 54141791, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 2-amino-2-(4-carboxy-3-methoxyphenyl)-3-(9H-xanthen-9-yl)propanoic acid (140 mg, 0.33 mmol) in dry dichloromethane (10 ml) was added a solution of boron tribromide in dichloromethane (1.0M, 0.7 ml). The resulting suspension was stirred at room temperature for 3 days, diluted with water and stirred a further 2 h. The dichloromethane layer was separated and the aqueous phase purified by ion exchange as described in Example 1 (vi). The water-tetrahydrofuran fractions were found to contain the desired product and were combined, evaporated and freeze-dried from water to give the title compound as a white powder, m.p. 191°-194° C.

Workup

  1. stirringstirred a further 2 h
  2. customThe dichloromethane layer was separated
  3. customthe aqueous phase purified by ion exchange
  4. customevaporated
  5. dry with materialfreeze-dried from water

Sources & evidence

ORD record
ord-3e82e25392804d83a27e067c85009c4e
Source dataset
uspto-grants-1999_04
Patent number
US05891899

Reaction notes

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