Boron tribromide → HCID 22839440, compound

HRID 35290Notes

Reaction equation

HRID 35290 reaction equation
C([O:3][C:4](=[O:42])[C:5](C(OCC)=O)([CH2:10][C:11]1[CH:16]=[C:15]([Cl:17])[C:14]([S:18][C:19]2[CH:24]=[CH:23][C:22]([O:25]C)=[C:21]([CH2:27][C:28]3[CH:29]=[N:30][C:31]([O:34]C)=[CH:32][CH:33]=3)[CH:20]=2)=[C:13]([Cl:36])[CH:12]=1)[NH:6]C(=O)C)C.B(Br)(Br)Br>ClCCl>[OH:25][C:22]1[CH:23]=[CH:24][C:19]([S:18][C:14]2[C:15]([Cl:17])=[CH:16][C:11]([CH2:10][C@@H:5]([C:4]([OH:42])=[O:3])[NH2:6])=[CH:12][C:13]=2[Cl:36])=[CH:20][C:21]=1[CH2:27][C:28]1[CH:33]=[CH:32][C:31](=[O:34])[NH:30][CH:29]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 14673543HCID 14673543, compound

Product 1

HCID 22839440HCID 22839440, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (-74°) solution of N-acetyl-3,5-dichloro-4-(4'-methoxy-3'-(6-methoxy-3-pyridylmethyl)-phenylthio)-α-carbethoxy-phenylalanine ethyl ester (0.39 g) in dry dichloromethane (10 ml) was added boron tribromide (0.58 ml) with stirring. The mixture was stirred whilst warming to room temperature and stirred for 5 hours. The reaction mixture was worked up and refluxed with concentrated hydrochloric in glacial acetic acid in a manner similar to that as described in Example 1 to afford DL-4-(4'-Hydroxy-3'-(6-oxo-3(1H)-pyridylmethyl) phenylthio)-3,5-dichlorophenylalanine as a cream solid (0.20 g, 70%), m.p. 261°-264°.

Workup

  1. stirringThe mixture was stirred
  2. stirringstirred for 5 hours
  3. temperaturerefluxed
  4. concentrationwith concentrated hydrochloric in glacial acetic acid in a manner similar to

Sources & evidence

ORD record
ord-65dcf63eb157458ea770ea5d09cb9989
Source dataset
uspto-grants-1988_08
Patent number
US04766121

Reaction notes

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