Glycine tert-butyl ester hydrochloride → Tert-butyl ({[5-(benzyloxy)-6-methyl-2-(piperidin-4-ylmethyl)pyrimidin-4-yl]carbonyl}amino)acetate hydrochloride

HRID 1626805Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:10]([C:30](OC(C)(C)C)=[O:31])=[N:11][C:12]([CH2:16][CH:17]2[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]2)=[N:13][C:14]=1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC1[C:46]([C:73]([O:75][C:76]([CH3:79])([CH3:78])[CH3:77])=[O:74])=[N:47]C(CC2CCN(C3C=CC(C4C=CC(CO)=CC=4)=CC=3)CC2)=NC=1C)C1C=CC=CC=1.[ClH:80].C(OC(=O)CN)(C)(C)C>>[ClH:80].[C:76]([O:75][C:73](=[O:74])[CH2:46][NH:47][C:30]([C:10]1[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:14]([CH3:15])[N:13]=[C:12]([CH2:16][CH:17]2[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]2)[N:11]=1)=[O:31])([CH3:79])([CH3:78])[CH3:77]

Participants

Reactant 3

HCID 2725036Glycine tert-butyl ester hydrochloride

HCID 58257700tert-Butyl 5-(benzyloxy)-2-{[1-(tert-butoxycarbonyl)piperidin-4-yl]methyl}-6-methylpyrimidine-4-carboxylate

HCID 68193244tert-Butyl 5-(benzyloxy)-2-{(1-[4'-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidine-4-carboxylate

Product 1

HCID 86670085Tert-butyl ({[5-(benzyloxy)-6-methyl-2-(piperidin-4-ylmethyl)pyrimidin-4-yl]carbonyl}amino)acetate hydrochlorideYield 72%

Procedure

In accordance with Examples 1-(11) and 1-(7), but using tert-butyl 5-(benzyloxy)-2-{[1-(tert-butoxycarbonyl)piperidin-4-yl]methyl}-6-methylpyrimidine-4-carboxylate obtained in Example 1-(6) instead of tert-butyl 5-(benzyloxy)-2-{(1-[4′-(hydroxymethyl)biphenyl-4-yl]piperidin-4-yl}methyl)-6-methylpyrimidine-4-carboxylate, and glycine tert-butyl ester hydrochloride instead of glycine ethyl ester hydrochloride, the title compound (yield 72%) was afforded as a white solid.

Sources & evidence

ORD record: ord-53283ad676a04595a7b92b173d482e38
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785462B2

Reaction notes

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