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

HRID 517592Notes

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][CH2:25][CH:26]([CH3:28])[CH3:27])=[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][CH2:25][CH:26]([CH3:28])[CH3:27])[C:5](=[O:20])[S:6]/2)=[CH:12][CH:13]=1)[CH3:19]

Participants

Reactant 4

HCID 62365Isobutyl chloroformate

HCID 81531Diisopropylethylamine

HCID 1249836(Z)-3-(2-aminoethyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione

HCID 45485995(Z)-N-(2-(5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)ethyl)acetamide

Product 1

HCID 71697448(Z)-isobutyl (2-(5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)ethyl)carbamate

Procedure

The title compound 26c was prepared from compound 76 (70 mg, 0.17 mmol), isobutyl chloroformate (25 μL, 0.19 mmol) and DIPEA (75 μL, 0.43 mmol) in a manner similar to that described for 25a in 96.4% (65 mg) yield as a light-yellow solid.

Workup

customyield as a light-yellow solid

Sources & evidence

ORD record: ord-9730467e9dde4962b6d4a1e1fc08e78e
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115122B2

Reaction notes

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