Chlorosuccinimide → 7-Chloro-6-((S)-2-methyl-pyrrolidine-1-carbonyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acid ((R)-1-phenyl-propyl)-amide

HRID 926404Notes

Reaction equation

[C:1]1([C@H:7]([NH:10][C:11]([C:13]2[CH:14]=[C:15]([C:22]([N:24]3[CH2:28][CH2:27][CH2:26][C@@H:25]3[CH3:29])=[O:23])[N:16]3[CH2:21][CH2:20][O:19][CH2:18][C:17]=23)=[O:12])[CH2:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:30]N1C(=O)CCC1=O>>[C:1]1([C@H:7]([NH:10][C:11]([C:13]2[C:14]([Cl:30])=[C:15]([C:22]([N:24]3[CH2:28][CH2:27][CH2:26][C@@H:25]3[CH3:29])=[O:23])[N:16]3[CH2:21][CH2:20][O:19][CH2:18][C:17]=23)=[O:12])[CH2:8][CH3:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Reactant 2

HCID 31398Chlorosuccinimide

HCID 716961256-[(2S)-2-methylpyrrolidine-1-carbonyl]-N-[(1R)-1-phenylpropyl]-1H,3H,4H-pyrrolo[2,1-c][1,4]oxazine-8-carboxamide

Product 1

HCID 897340927-Chloro-6-((S)-2-methyl-pyrrolidine-1-carbonyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acid ((R)-1-phenyl-propyl)-amide

Procedure

The compound was prepared from 6-((S)-2-methyl-pyrrolidine-1-carbonyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acid ((R)-1-phenyl-propyl)-amide (Comp. No. 16a) and N-chloro-succinimide in analogy to the synthesis of comp. no. 16ru. LC/MS (method 3): Rt=1.86 min; m/z=430.22 (M+H+).

Sources & evidence

ORD record: ord-ff9c5bb74f92478a9fb7389354e6b94c
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284333B2

Reaction notes

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