Sodium Ascorbate → HCID 118318756, compound

HRID 921090Notes

Reaction equation

HRID 921090 reaction equation
[CH2:1]([O:4][C:5]1([CH3:36])[CH2:10][CH2:9][N:8]([C:11]2[N:16]3[N:17]=[C:18]([CH2:20][N:21]=[N+:22]=[N-:23])[CH:19]=[C:15]3[N:14]=[C:13]([CH3:24])[C:12]=2[C@H:25]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:7][CH2:6]1)[CH:2]=[CH2:3].[CH2:37]([O:40][CH:41]([CH2:44][CH:45]([CH3:47])[CH3:46])[C:42]#[CH:43])[CH:38]=[CH2:39].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CO>[CH2:37]([O:40][CH:41]([C:42]1[N:23]=[N:22][N:21]([CH2:20][C:18]2[CH:19]=[C:15]3[N:14]=[C:13]([CH3:24])[C:12]([C@H:25]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:11]([N:8]4[CH2:9][CH2:10][C:5]([O:4][CH2:1][CH:2]=[CH2:3])([CH3:36])[CH2:6][CH2:7]4)[N:16]3[N:17]=2)[CH:43]=1)[CH2:44][CH:45]([CH3:47])[CH3:46])[CH:38]=[CH2:39]

Participants

5

Reactant 3

HCID 23667548Sodium AscorbateHCID 1183070893-(Allyloxy)-5-methylhex-1-yneHCID 118318736(S)-ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(azidomethyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate

Product 1

HCID 118318756HCID 118318756, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (S)-ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(azidomethyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (0.179 g, 0.358 mmol), 3-(allyloxy)-5-methylhex-1-yne (0.109 g, 0.717 mmol), Cu(II)SO4.5H2O (8.95 mg, 0.036 mmol) and (+)-sodium L-ascorbate (0.071 g, 0.358 mmol) in MeOH (2 mL) was stirred for 1 h at rt. Then, purified by prep-HPLC to afford (2S)-ethyl 2-(2-((4-(1-(allyloxy)-3-methylbutyl)-1H-1,2,3-triazol-1-yl)methyl)-7-(4-(allyloxy)-4-methylpiperidin-1-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (0.0921 g, 0.141 mmol, 39.4% yield) as pale yellow paste. LCMS (M+H)=652.7.

Workup

  1. customThen, purified by prep-HPLC

Sources & evidence

ORD record
ord-972cfb1a3ac94e10821e2ac9cdcebae9
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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