4-Tert-butyl 1-methyl 2-(benzyloxy)-3-hydroxyfumarate → HCID 178450817, compound

HRID 2169128Notes

Reaction equation

HRID 2169128 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]([NH2:18])=[NH:17].C[O:20][C:21](=O)/[C:22](/[O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[C:23](\O)/[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].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:27]([O:26][C:24]([C:23]1[C:22]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[C:21]([OH:20])[N:18]=[C:16]([CH2:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[Cl:2])[N:17]=1)=[O:25])([CH3:30])([CH3:28])[CH3:29]

Participants

4

Reactant 3

HCID 546790054-Tert-butyl 1-methyl 2-(benzyloxy)-3-hydroxyfumarateHCID 867257832-(2'-Chloro-biphenyl-2-yl)-acetamidine hydrochloride saltHCID 178450818HCID 178450818, compound

Product 1

HCID 178450817HCID 178450817, compoundYield 55.8%

Procedure

5-Benzyloxy-2-(2′-chloro-biphenyl-2-ylmethyl)-6-hydroxypyrimidine-4-carboxylic acid tert-butyl ester (6-02) (5 g, 55.8%) was synthesized as a brown solid from 2-(2′-chloro-biphenyl-2-yl)-acetamidine hydrochloride salt (5-02) (5 g, 17.82 mmol) and (E)-2-benzyloxy-3-hydroxy-but-2-enedioic acid 4-tert-butyl ester 1-methyl ester (4) (9.4 g, 30.73 mmol) 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-d9bddfb2eb8b4d4ab8a25090f3160ab2
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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