Triphenylphosphine → HCID 67360592, compound

HRID 1747459Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[C:12]([CH2:18]O)[CH:13]=[C:14]([Br:17])[CH:15]=2)[CH:10]=[C:9]1[O:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:28]([O:30][C:31](=[O:47])[CH2:32][CH:33]([N:37]1[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=2[NH:39][C:38]1=[O:46])[CH2:34][CH2:35][CH3:36])C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[C:12]([CH2:18][N:39]3[C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=4[N:37]([CH:33]([CH2:32][C:31]([O:30][CH3:28])=[O:47])[CH2:34][CH2:35][CH3:36])[C:38]3=[O:46])[CH:13]=[C:14]([Br:17])[CH:15]=2)[CH:10]=[C:9]1[O:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

6-Bromo-2-tert-butoxycarbonyloxy-4-hydroxymethyl-indole-1-carboxylic acid tert-butyl ester (220 mg, 0.50 mmol) is and 3-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-hexanoic acid ethyl ester (151 mg, 0.55 mmol) is taken up in 5 mL of tetrahydrofuran and then triphenyl phosphine is added (157 mg, 0.6 mmol). The reaction is stirred at 0° C. and diisopropyl azodicarboxylate (116 □L, 0.6 mmol) is added drop wise to the reaction. The reaction is stirred at room temperature for 4 hours and then the solvent evaporated in vacuo. Product is purified by preparative TLC 3% methanol in dichloromethane to give the title compound (200 mg 0.28 mmol 57%). LCMS (ESMS): m/z 687.7 (M+H+).

Workup

customwise to the reaction
stirringThe reaction is stirred at room temperature for 4 hours
customthe solvent evaporated in vacuo
customProduct is purified by preparative TLC 3% methanol in dichloromethane

Sources & evidence

ORD record: ord-ab465b190a8540cbab397c00aece0df0
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150556B2

Reaction notes

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