(2S)-Methyl 2-(7-(4-allyl-7-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-2-(2'-(but-3-en-1-yl)-[1,1'-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate → methyl (2S)-2-(4,32-dimethyl-29-oxa-5,7,8,26-tetrazaheptacyclo[24.6.2.16,9.110,14.02,7.015,20.030,34]hexatriaconta-1(33),2,4,6(36),8,10,12,14(35),15,17,19,23,30(34),31-tetradecaen-3-yl)-2-[(2-methylpropan-2-yl)oxy]acetate

HRID 1400709Notes

Reaction equation

HRID 1400709 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][O:7][C:6]2[CH:10]=[C:11]([CH3:50])[C:12]([C:14]3[N:19]4[N:20]=[C:21]([C:23]5[CH:24]=[C:25]([C:29]6[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=6[CH2:35][CH2:36][CH:37]=[CH2:38])[CH:26]=[CH:27][CH:28]=5)[CH:22]=[C:18]4[N:17]=[C:16]([CH3:39])[C:15]=3[C@H:40]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])[C:41]([O:43][CH3:44])=[O:42])=[CH:13][C:5]1=2)C=C>ClCCCl.CC1C=C(C)C(N2C(=[Ru](Cl)(Cl)=CC3C(OC(C)C)=CC=CC=3)N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1>[C:46]([O:45][C@@H:40]([C:15]1[C:16]([CH3:39])=[N:17][C:18]2=[CH:22][C:21]3=[N:20][N:19]2[C:14]=1[C:12]1[CH:13]=[C:5]2[C:6]([O:7][CH2:8][CH2:9][N:4]2[CH2:1][CH:38]=[CH:37][CH2:36][CH2:35][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[C:25]2[CH:24]=[C:23]3[CH:28]=[CH:27][CH:26]=2)=[CH:10][C:11]=1[CH3:50])[C:41]([O:43][CH3:44])=[O:42])([CH3:49])([CH3:48])[CH3:47]

Participants

4

Reactant 1

HCID 86710760(2S)-Methyl 2-(7-(4-allyl-7-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-2-(2'-(but-3-en-1-yl)-[1,1'-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate

Product 1

HCID 86710762methyl (2S)-2-(4,32-dimethyl-29-oxa-5,7,8,26-tetrazaheptacyclo[24.6.2.16,9.110,14.02,7.015,20.030,34]hexatriaconta-1(33),2,4,6(36),8,10,12,14(35),15,17,19,23,30(34),31-tetradecaen-3-yl)-2-[(2-methylpropan-2-yl)oxy]acetate

Reagents, catalysts & solvents 2

HCID 11763533(1,3-Bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene)(dichloro)((2-((propan-2-yl)oxy)phenyl)methylidene)rutheniumCatalystHCID 111,2-DichloroethaneSolvent

Procedure

A solution of (2S)-methyl 2-(7-(4-allyl-7-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-2-(2′-(but-3-en-1-yl)-[1,1′-biphenyl]-3-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (0.030 g, 0.045 mmol) in dry DCE (5 mL) was heated (70° C. oil bath) and then treated with Hoveyda-Grubbs Cat. 2nd Gen. (3 mg, 5 μmol). The reaction was stirred for 90 min. The solvent was removed and the intermediate was used immediately in the following step. LCMS (M+H)=643.4.

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-6731a6ff097247c4b59bb073ee723242
Source dataset
uspto-grants-2014_12
Patent number
US08906929B2

Reaction notes

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