Isobutyl chloroformate → N-(1-ethyl-2-pyrrolidylmethyl)-8-acetamino-1,4-benzodioxane-5-carboxamide

HRID 2286966Notes

Reaction equation

[NH:1]([C:5]1[C:10]2[O:11][CH2:12][CH2:13][O:14][C:9]=2[C:8]([C:15]([OH:17])=O)=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3].ClC(OCC(C)C)=O.[CH2:26]([N:28]1[CH2:32][CH2:31][CH2:30][CH:29]1[CH2:33][NH2:34])[CH3:27]>>[CH2:26]([N:28]1[CH2:32][CH2:31][CH2:30][CH:29]1[CH2:33][NH:34][C:15]([C:8]1[C:9]2[O:14][CH2:13][CH2:12][O:11][C:10]=2[C:5]([NH:1][C:2]([CH3:4])=[O:3])=[CH:6][CH:7]=1)=[O:17])[CH3:27]

Participants

Reactant 3

HCID 62365Isobutyl chloroformate

HCID 1172952-Aminomethyl-1-ethylpyrrolidine

HCID 149562078-Acetamido-1,4-benzodioxan-5-carboxylic acid

Product 1

HCID 20544727N-(1-ethyl-2-pyrrolidylmethyl)-8-acetamino-1,4-benzodioxane-5-carboxamide

Procedure

According to the method described in Example 31, the 8-acetamino-1,4-benzodioxane-5-carboxylic acid was treated with isobutyl chloroformate and 1-ethyl-2-aminomethylpyrrolidine. N-(1-ethyl-2-pyrrolidylmethyl)-8-acetamino-1,4-benzodioxane-5-carboxamide was obtained. The structure was confirmed by nuclear magnetic resonance analysis.

Sources & evidence

ORD record: ord-00d8b82c5a7f4ade869bf32ee9785777
Source dataset: uspto-grants-1981_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04268512

Reaction notes

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