H-D-Pro-otbu → (R)-tert-butyl 1-(4-((2-amino-4-(mesitylsulfonyloxy)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)pyrrolidine-2-carboxylate

HRID 2207099Notes

Reaction equation

HRID 2207099 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[S:10]([O:13][C:14]1[C:19]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27]Cl)=[CH:23][C:22]=2[O:29][CH3:30])=[C:18]([CH3:31])[N:17]=[C:16]([NH2:32])[N:15]=1)(=[O:12])=[O:11].[NH:33]1[CH2:37][CH2:36][CH2:35][C@@H:34]1[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39]>>[NH2:32][C:16]1[N:15]=[C:14]([O:13][S:10]([C:3]2[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[CH3:1])(=[O:11])=[O:12])[C:19]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][N:33]3[CH2:37][CH2:36][CH2:35][C@@H:34]3[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[CH:23][C:22]=2[O:29][CH3:30])=[C:18]([CH3:31])[N:17]=1

Participants

3

Reactant 2

HCID 6931635H-D-Pro-otbuHCID 879450752-Amino-5-(4-(chloromethyl)-2-methoxybenzyl)-6-methylpyrimidin-4-yl 2,4,6-trimethylbenzenesulfonate

Product 1

HCID 117992851(R)-tert-butyl 1-(4-((2-amino-4-(mesitylsulfonyloxy)-6-methylpyrimidin-5-yl)methyl)-3-methoxybenzyl)pyrrolidine-2-carboxylateYield 91.2%

Procedure

The sub-title compound was synthesized by the method of example 1 step (vii) from the product of example 1 step (v) (200 mg) and (R)-tert-butyl pyrrolidine-2-carboxylate (108 mg). The sub-title compound (234 mg) was obtained as a colourless amorphous solid; LC-MS: m/z 611.

Sources & evidence

ORD record
ord-ab9689290c5d4941adc758513fed9bda
Source dataset
uspto-grants-2016_06
Patent number
US09376398B2

Reaction notes

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