tert-Butoxy bis(dimethylamino)methane → 4-(3-Dimethylamino-2-methoxymethyl-acryloyl)-1H-pyrrole-2-carboxylic Acid (2-hydroxy-1-(S)-phenyl-ethyl)-amide

HRID 852304Notes

Reaction equation

HRID 852304 reaction equation
[OH:1][CH2:2][C@@H:3]([NH:10][C:11]([C:13]1[NH:14][CH:15]=[C:16]([C:18](=[O:23])[CH2:19][CH2:20][O:21][CH3:22])[CH:17]=1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CC(O[CH:29](N(C)C)[N:30]([CH3:32])[CH3:31])(C)C>C1COCC1>[OH:1][CH2:2][C@@H:3]([NH:10][C:11]([C:13]1[NH:14][CH:15]=[C:16]([C:18](=[O:23])[C:19]([CH2:20][O:21][CH3:22])=[CH:29][N:30]([CH3:32])[CH3:31])[CH:17]=1)=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 600906044-(3-Methoxy-propionyl)-1H-pyrrole-2-carboxylic acid (2-hydroxy-1-(S)-phenyl-ethyl)-amide

Product 1

HCID 865879764-(3-Dimethylamino-2-methoxymethyl-acryloyl)-1H-pyrrole-2-carboxylic Acid (2-hydroxy-1-(S)-phenyl-ethyl)-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(3-Methoxy-propionyl)-1H-pyrrole-2-carboxylic acid (2-hydroxy-1-(S)-phenyl-ethyl)-amide was treated with an excess of Bredereck's reagent in THF at room temperature to 50° C. for 3 days. The solvent was removed under reduced pressure and the concentrate was used directly in the next step. HPLC Method B, Rt=5.0 minutes “broad peak”.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-7bb57d3f7ef44a8ba94ae9fb4fe8c9fa
Source dataset
uspto-grants-2007_08
Patent number
US07253187B2

Reaction notes

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