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Dimethylformamide → N-(4-benzyloxy-5-fluoro-2-nitrophenyl)glycine ethyl ester

HRID 1870210
Notes
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Reaction equation

HRID 1870210 reaction equation
[F:1][C:2]1[CH:7]=[C:6](F)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C.CN(C=O)C.Cl.[CH2:33]([O:35][C:36](=[O:39])[CH2:37][NH2:38])[CH3:34]>C1COCC1>[CH2:33]([O:35][C:36](=[O:39])[CH2:37][NH:38][C:6]1[CH:7]=[C:2]([F:1])[C:3]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10])[CH3:34]
ParticipantsProcedureSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 186954361-(Benzyloxy)-2,4-difluoro-5-nitrobenzene

Product 1

HCID 18695453N-(4-benzyloxy-5-fluoro-2-nitrophenyl)glycine ethyl esterYield 8%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

By using 4.41 g of benzyl 2,4-difluoro-5-nitrophenyl ether, 5.05 g of triethylamine, 30 ml of DMF, 30 ml of THF and 2.32 g of glycine ethyl ester hydrochloride, 454 mg (8%) of N-(4-benzyloxy-5-fluoro-2-nitrophenyl)glycine ethyl ester was obtained.

Sources & evidence

ORD record
ord-036383ab067c48c3bf432425603216b2
Source dataset
uspto-grants-2000_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06096743

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes