Triphenylphosphine → HCID 86633491, compound

HRID 1255171Notes

Reaction equation

[OH:1][CH2:2][C:3]1[CH:36]=[CH:35][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[N:20]=[C:19]([N:21]3[C:25]([C:26]([F:29])([F:28])[F:27])=[C:24]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:23]=[N:22]3)[CH:18]=[CH:17][CH:16]=2)=[CH:5][CH:4]=1.O[C:38]1[CH:43]=[CH:42][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:40][CH:39]=1.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>C1COCC1>[F:28][C:26]([F:29])([F:27])[C:25]1[N:21]([C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[O:8][CH2:7][C:6]3[CH:5]=[CH:4][C:3]([CH2:2][O:1][C:38]4[CH:43]=[CH:42][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:40][CH:39]=4)=[CH:36][CH:35]=3)[N:20]=2)[N:22]=[CH:23][C:24]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of the title compound from Example 7 Step A (30.0 mg, 0.060 mmol) and 4-hydroxybenzotrifluoride (29.3 mg, 0.181 mmol) in THF (0.400 mL) were added triphenylphosphine (47.5 mg, 0.181 mmol) and diisopropyl azodicarboxylate (0.035 mL, 0.181 mmol). The resulting mixture was stirred at 60° C. After 3.5 h, the mixture was allowed to cool to ambient temperature, then was concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 50% EtOAc in hexanes, then 50 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 642.3 [M+H]+.

Workup

temperatureto cool to ambient temperature
concentrationwas concentrated in vacuo
customPurification by flash chromatography on silica gel (0 to 50% EtOAc in hexanes

Sources & evidence

ORD record: ord-0ba51b5bbd5142aeb5d91fa96faaff2a
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455638B2

Reaction notes

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