4-Tert-butyl 1-methyl 2-(benzyloxy)-3-hydroxyfumarate → HCID 178450806, compound

HRID 2169159Notes

Reaction equation

HRID 2169159 reaction equation
Cl.[C:2]1([C:8]2([CH2:13][C:14]([NH2:16])=[NH:15])[CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O:18][C:19](=O)/[C:20](/[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[C:21](\O)/[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].C(OC(C1C(OCC2C=CC=CC=2)=C(O)N=C(CC2C=CC=CC=2C2C=CC=CC=2)N=1)=O)(C)(C)C>>[C:25]([O:24][C:22]([C:21]1[C:20]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[C:19]([OH:18])[N:16]=[C:14]([CH2:13][C:8]2([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:12][CH2:11][CH2:10][CH2:9]2)[N:15]=1)=[O:23])([CH3:28])([CH3:26])[CH3:27]

Participants

4

Reactant 3

HCID 546790054-Tert-butyl 1-methyl 2-(benzyloxy)-3-hydroxyfumarateHCID 867258072-(1-Phenyl-cyclopentyl)-acetamidine HCl saltHCID 178450818HCID 178450818, compound

Product 1

HCID 178450806HCID 178450806, compoundYield 51.8%

Procedure

5-Benzyloxy-6-hydroxy-2-(1-phenyl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid tert-butyl ester (27-01) (4.5 g, 51.8%) was synthesized from 2-(1-phenyl-cyclopentyl)-acetamidine HCl salt (26-01) (4.5 g, 18.86 mmol) and (E)-2-benzyloxy-3-hydroxy-but-2-enedioic acid 4-tert-butyl ester 1-methyl ester (4) (10.2 g, 33.41 mmol) as a yellow solid following the procedure as described for 5-benzyloxy-2-biphenyl-2-ylmethyl-6-hydroxypyrimidine-4-carboxylic acid tert-butyl ester (6-01).

Sources & evidence

ORD record
ord-8e6930f80f06466998478e093fdf36cc
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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