Ethyl chloroformate → 1,3-Dimethyl-4-pyrrolidinoacetyl-1,4,9,10-tetrahydropyrrolo[3,2-b][1,5]benzodiazepin-10-one

HRID 1902490

Reaction equation

ClC(OCC)=O.[N:7]1([CH2:12][C:13]([OH:15])=O)[CH2:11][CH2:10][CH2:9][CH2:8]1.[CH3:16][N:17]1[C:26]2[C:25](=[O:27])[NH:24][C:23]3[CH:28]=[CH:29][CH:30]=[CH:31][C:22]=3[NH:21][C:20]=2[C:19]([CH3:32])=[CH:18]1.[OH-].[Na+]>O1CCCC1>[CH3:16][N:17]1[C:26]2[C:25](=[O:27])[NH:24][C:23]3[CH:28]=[CH:29][CH:30]=[CH:31][C:22]=3[N:21]([C:13](=[O:15])[CH2:12][N:7]3[CH2:8][CH2:9][CH2:10][CH2:11]3)[C:20]=2[C:19]([CH3:32])=[CH:18]1

Participants

Conditions

Temperature: 0 °C

Procedure

1.1 g of ethyl chloroformate are added dropwise at 0° C. to a suspension of 1.29 g of pyrrolidin-1-ylacetic acid in 20 ml of tetrahydrofuran. 2.28 g of 1,3-dimethyl-1,4,9,10-tetrahydropyrrolo[3,2-b][1,5]benzodiazepin-10-one are added to the obtained suspension. The mixture is stirred 1 hour at 0° C. and a further 4 hours at room temperature. It is then poured onto 160 ml of 2 N sodium hydroxide solution and extracted with toluene. The organic phase is concentrated to dryness. The residue is chromatographed over a silica gel column by means of a mixture of dioxane/methanol (1:1) to yield 2.1 g of the title compound of m.p. 210° to 212° C. (from isopropanol).

Workup

extractionextracted with toluene
concentrationThe organic phase is concentrated to dryness
customThe residue is chromatographed over a silica gel column by means of a mixture of dioxane/methanol (1:1)

Sources & evidence

ORD record: ord-bdcd95f8e4ee4586a6e00e95cb8c3b04
Source dataset: uspto-grants-1982_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04363816

Linked notes

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