Boron tribromide → HCID 16034837, compound

HRID 2387675Notes

Reaction equation

B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]([CH:37]=[CH:38][CH:39]=1)[O:10][C@H:11]1[CH2:15][CH2:14][N:13]([C:16]([CH3:36])([CH3:35])[CH2:17][CH2:18][C:19]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:20]([NH2:22])=[O:21])[CH2:12]1>ClCCl>[OH:6][C:7]1[CH:8]=[C:9]([CH:37]=[CH:38][CH:39]=1)[O:10][C@H:11]1[CH2:15][CH2:14][N:13]([C:16]([CH3:36])([CH3:35])[CH2:17][CH2:18][C:19]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:20]([NH2:22])=[O:21])[CH2:12]1

Participants

Conditions

Temperature: 0 °C

Procedure

Boron tribromide (1M in dichloromethane, 20.7 mL, 20.7 mmol) was added to an ice-cooled solution of the product of example 6 (2.45 g, 5.18 mmol) in dichloromethane (25 mL) and the mixture was stirred at 0° C. for 20 minutes. The reaction was then quenched with 0.88 ammonia solution and stirred at room temperature for 20 minutes. The reaction mixture was extracted with dichloromethane (3×25 mL) and the combined organic solution was dried over sodium sulfate and concentrated in vacuo. Purification of the residue by column chromatography on silica gel, eluting with pentane:ethyl acetate/methanol/0.88 ammonia (90:10:1), 50:50 to 33:66, afforded the title compound as a white foam in 60% yield, 1.42 g.

Workup

customThe reaction was then quenched with 0.88 ammonia solution
stirringstirred at room temperature for 20 minutes
extractionThe reaction mixture was extracted with dichloromethane (3×25 mL)
dry with materialthe combined organic solution was dried over sodium sulfate
concentrationconcentrated in vacuo
customPurification of the residue by column chromatography on silica gel
washeluting with pentane

Sources & evidence

ORD record: ord-f581af7b2f514fbc87e82b08c436d178
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268881B2

Reaction notes

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