Triphenylphosphine → HCID 123711222, compound

HRID 921156Notes

Reaction equation

HRID 921156 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:13]([CH3:47])=[N:14][C:15]2[N:16]([N:33]=[C:34]([CH:36]=[CH:37][CH2:38][C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][C:40]=3O)[CH:35]=2)[C:17]=1[N:18]1[CH2:23][CH2:22][C:21]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][C@H:30]([OH:32])[CH3:31])([CH3:24])[CH2:20][CH2:19]1)[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([O:5][C@@H:6]([C:12]1[C:13]([CH3:47])=[N:14][C:15]2=[CH:35][C:34]3=[N:33][N:16]2[C:17]=1[N:18]1[CH2:23][CH2:22][C:21]([CH3:24])([O:25][CH2:26][CH2:27][CH2:28][CH2:29][C@H:30]([CH3:31])[O:32][C:44]2[CH:43]=[C:42]([F:45])[CH:41]=[CH:40][C:39]=2[CH2:38][CH:37]=[CH:36]3)[CH2:20][CH2:19]1)[C:7]([OH:9])=[O:8])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 123712807HCID 123712807, compound

Product 1

HCID 123711222HCID 123711222, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-ethyl 2-(tert-butoxy)-2-(2-(3-(4-fluoro-2-hydroxyphenyl)prop-1-en-1-yl)-7-(4-(((R)-5-hydroxyhexyl)oxy)-4-methylpiperidin-1-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (240 mg, 0.367 mmol) in THF (50 mL) at 0° C. was added Ph3P (144 mg, 0.550 mmol) followed by DEAD (0.087 mL, 0.550 mmol) and the resulting mixture was stirred at room temp for 3 h. At this point LCMS indicated completion of reaction and desired product as mixture of four isomers. Water (25 mL) was then added and the mixture was extracted with ether (50 mL), dried (Na2SO4), filtered and concentrated. The residue was then purified by Biotage (0-30% EtOAc/hexane) to afford to afford desired ester (165 mg, 0.259 mmol, 70.7% yield) as a inseparable mixture of two isomers which was used in the next step without further purification. LCMS (M+H)=637.3

Sources & evidence

ORD record
ord-4073a70b1d4649ea8fb4469961d1d5f7
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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