Methyl chloroformate → (Z)-methyl (2-(5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)ethyl)carbamate

HRID 517591Notes

Reaction equation

HRID 517591 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])/[C:7](=[CH:10]/[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH3:19])=[CH:13][CH:12]=2)/[S:6][C:5]1=[O:20].Cl[C:22]([O:24][CH3:25])=[O:23].CCN(C(C)C)C(C)C.C(OC1C=CC(/C=C2/C(=O)N(CCNC(=O)C)C(=O)S/2)=CC=1)C>>[CH2:18]([O:17][C:14]1[CH:15]=[CH:16][C:11](/[CH:10]=[C:7]2/[C:8](=[O:9])[N:4]([CH2:3][CH2:2][NH:1][C:22](=[O:23])[O:24][CH3:25])[C:5](=[O:20])[S:6]/2)=[CH:12][CH:13]=1)[CH3:19]

Participants

5

Reactant 4

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 1249836(Z)-3-(2-aminoethyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dioneHCID 45485995(Z)-N-(2-(5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)ethyl)acetamide

Product 1

HCID 71697446(Z)-methyl (2-(5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)ethyl)carbamate

Procedure

The title compound 26a was prepared from compound 76 (101 mg, 0.25 mmol), methyl chloroformate (21 μL, 0.28 mmol) and DIPEA (131 μL, 0.75 mmol) in a manner similar to that described for 25a in 98.2% (86 mg) yield as a yellow solid.

Workup

  1. customyield as a yellow solid

Sources & evidence

ORD record
ord-bf531a6b48d84a09b39489cdc2c3af11
Source dataset
uspto-grants-2015_08
Patent number
US09115122B2

Reaction notes

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