Boron tribromide → Ammonia

HRID 500621Notes

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

Reactant 2

HCID 25134Boron tribromide

HCID 59423961HCID 59423961, compound

Product 2

HCID 222Ammonia

HCID 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

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

Sources & evidence

ORD record: ord-b27a38874efe46da9f5150e1c06f9e4b
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772223B2

Reaction notes

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