Triphenylphosphine → HCID 44124835, compound

HRID 1922309Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@H:6]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:5]2.[N:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][CH2:25][CH2:26]O)[CH:19]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[N:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][CH2:25][CH2:26][O:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[CH2:7][C@H:6]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:5]3)[CH:19]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of N-[(2S)-5-hydroxy-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide (50 mg, 0.196 mmol, Description 3) and 3-pyridinepropanol (0.028 ml, 0.215 mmol) in dichloromethane (1 ml) was added diisopropyl azodicarboxylate (0.038 ml, 0.196 mmol) followed by triphenylphosphine (51.4 mg, 0.196 mmol). The reaction mixture was stirred at 25° C. overnight. Solvent was removed under vacuum and the crude product was purified by reverse phase chromatography using the MDAP. Relevant fractions were combined and concentrated to give 34 mg of material which was dried in the vacuum oven overnight. This solid was then dissolved in DCM (10 ml) and washed with water (2*10 ml). The organic phase was dried over MgSO4 and concentrated. This product was purified by MDAP a second time. This material was dissolved in MeOH and loaded on to a SCX cartridge, washed with MeOH and eluted with methanolic ammonia. Relevant fractions were combined and concentrated to give the title compound as a white solid (2 mg).

Workup

customSolvent was removed under vacuum
customthe crude product was purified by reverse phase chromatography
concentrationconcentrated

Sources & evidence

ORD record: ord-7dd1e592eec34a0381d2b452c4b83484
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173820B2

Reaction notes

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