4-Tert-butyl 1-methyl 2-(benzyloxy)-3-hydroxyfumarate → HCID 178450811, compound

HRID 2169160Notes

Reaction equation

HRID 2169160 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH2:14][C:15]([NH2:17])=[NH:16])[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C[O:19][C:20](=O)/[C:21](/[O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[C:22](\O)/[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].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:26]([O:25][C:23]([C:22]1[C:21]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[C:20]([OH:19])[N:17]=[C:15]([CH2:14][C:9]2([C:6]3[CH:5]=[CH:4][C:3]([Cl:2])=[CH:8][CH:7]=3)[CH2:13][CH2:12][CH2:11][CH2:10]2)[N:16]=1)=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

4

Reactant 3

HCID 546790054-Tert-butyl 1-methyl 2-(benzyloxy)-3-hydroxyfumarateHCID 867258092-[1-(4-chlorophenyl)-cyclopentyl]-acetamidine HCl saltHCID 178450818HCID 178450818, compound

Product 1

HCID 178450811HCID 178450811, compoundYield 55.1%

Procedure

5-Benzyloxy-2-[1-(4-chlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid tert-butyl ester (27-02) (12 g, 55%) was synthesized from [1-(4-chlorophenyl)-cyclopentyl]-acetonitrile (26-02) (12 g, 44.03 mmol) and (E)-2-benzyloxy-3-hydroxy-but-2-enedioic acid 4-tert-butyl ester 1-methyl ester (4) (23.49 g, 76.27 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-3786a07d81604e2d9163e153cf9405d5
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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