Phosphorus tribromide → HCID 66684104, compound

HRID 579200Notes

Reaction equation

HRID 579200 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:24]#[C:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:8][C:9]=1[N:10]1[C@H:15]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:14][CH2:13][C@H:12](O)[C:11]1=[O:23])=[O:4].P(Br)(Br)[Br:31]>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:24]#[C:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:8][C:9]=1[N:10]1[CH:15]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:14][CH2:13][C@H:12]([Br:31])[C:11]1=[O:23])=[O:4]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 66684775HCID 66684775, compound

Product 1

HCID 66684104HCID 66684104, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-((3S,6S)-6-cyclohexyl-3-hydroxy-2-oxo-piperidin-1-yl)-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester (200 mg, 0.75 mmol, 1 equiv) in CH2Cl2 (1.0 mL) was added PBr3 (1.0 M in CH2Cl2, 0.09 ml, 0.38 mmol, 0.8 equiv.) at room temperature and the resulting solution was stirred at room temperature for 18 hours. The reaction solution was then concentrated under vacuum and the residue was purified by silica gel column chromatography, (EtOAc/Heptane, 10%˜60%) to give product 166 mg (yield 76%). MS: 481 [M+H+].

Workup

  1. concentrationThe reaction solution was then concentrated under vacuum
  2. customthe residue was purified by silica gel column chromatography, (EtOAc/Heptane, 10%˜60%)

Sources & evidence

ORD record
ord-ccb8b8155ce84ce0ad7cee3a77b8fa0d
Source dataset
uspto-grants-2015_05
Patent number
US09040690B2

Reaction notes

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