Boron tribromide → Ammonia

HRID 2387679Notes

Reaction equation

HRID 2387679 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:32]=[C:33]([O:35]C)[CH:34]=1)[O:5][C@H:6]1[CH2:10][CH2:9][N:8]([C:11]([CH3:31])([CH3:30])[CH2:12][CH2:13][C:14]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]([NH2:17])=[O:16])[CH2:7]1.B(Br)(Br)Br>>[F:1][C:2]1[CH:3]=[C:4]([CH:32]=[C:33]([OH:35])[CH:34]=1)[O:5][C@H:6]1[CH2:10][CH2:9][N:8]([C:11]([CH3:30])([CH3:31])[CH2:12][CH2:13][C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:15]([NH2:17])=[O:16])[CH2:7]1.[NH3:8]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 59423961HCID 59423961, compound

Product 2

HCID 222AmmoniaHCID 16065264HCID 16065264, compound

Procedure

The title compound was prepared from the product of example 45, using the same method as that described for example 34, with the addition of further boron tribromide (1M in dichloromethane, 4 eq) after 3 hours, and subsequent stirring for 2 hrs. Crude material was purified by column chromatography on silica gel, eluting with ethyl acetate:methanol:0.88 ammonia, 98:2:0.2 to 94:6:0.6 to afford a white foam in 35% yield.

Workup

  1. customCrude material was purified by column chromatography on silica gel
  2. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-7890aaba2d74444ebd5ad3b3a7bfa966
Source dataset
uspto-grants-2012_09
Patent number
US08268881B2

Reaction notes

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