Benzocaine → HCID 123769555, compound

HRID 56872Notes

Reaction equation

HRID 56872 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][CH:21]([N:25]1[CH:30]=[C:29]([O:31][CH3:32])[C:28]([C:33]2[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:34]=2[C:40]#[N:41])=[CH:27][C:26]1=[O:42])[C:22]([OH:24])=O)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:43][C:44]1[CH:54]=[CH:53][C:47]([C:48]([O:50][CH2:51][CH3:52])=[O:49])=[CH:46][CH:45]=1.CC(C)N=C=NC(C)C>CN(C)C=O>[Si:1]([O:18][CH2:19][CH2:20][CH:21]([N:25]1[CH:30]=[C:29]([O:31][CH3:32])[C:28]([C:33]2[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:34]=2[C:40]#[N:41])=[CH:27][C:26]1=[O:42])[C:22]([NH:43][C:44]1[CH:45]=[CH:46][C:47]([C:48]([O:50][CH2:51][CH3:52])=[O:49])=[CH:53][CH:54]=1)=[O:24])([C:14]([CH3:16])([CH3:17])[CH3:15])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 12734DiisopropylcarbodiimideHCID 1239123964-{[tert-Butyl(diphenyl)silyl]oxy}-2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoic acid

Product 1

HCID 123769555HCID 123769555, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

565 mg (940 μmol) of 4-{[tert-butyl(diphenyl)silyl]oxy}-2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoic acid (racemate), 155 mg (940 μmol) of ethyl 4-aminobenzoate, 134 mg (940 μmol) of Oxima and 146 μl (940 μmol) of DIC in 19 ml of dimethylformamide were reacted according to General Method 5B. The crude product was purified by flash chromatography (120 g cartridge, 85 ml/min, cyclohexane/ethyl acetate gradient). Yield: 268 mg (38% of theory)

Workup

  1. customThe crude product was purified by flash chromatography (120 g cartridge, 85 ml/min, cyclohexane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-f6f9939b854d48d2b32ebb7d2acb3c4c
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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