Ethyl 2-bromopropionate → HCID 21955415, compound

HRID 2213146Notes

Reaction equation

HRID 2213146 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[CH:5]([CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:4]2[CH:21]=[CH:22][CH:23]=[CH:24][C:3]1=2.CC([O-])(C)C.[K+].Br[CH:32]([CH3:38])[C:33]([O:35][CH2:36][CH3:37])=[O:34]>CN(C=O)C.C(Cl)Cl>[C:17]([O:16][C:14](=[O:15])[CH2:13][CH:5]1[C:4]2[CH:21]=[CH:22][CH:23]=[CH:24][C:3]=2[C:2](=[O:1])[N:8]([CH2:38][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]1=2)([CH3:19])([CH3:20])[CH3:18]

Participants

6

Reactant 3

HCID 79040Ethyl 2-bromopropionate2×HCID 23665647Potassium tert-butoxide2×HCID 86760239HCID 86760239, compound

Product 1

HCID 21955415HCID 21955415, compoundYield 45.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (6-oxo-6,11-dihydro-5H-dibenzo[b,e]azepin-11-yl)acetate 4 (2 g, 6.18 mmol) was dissolved in 25 ml of dry DMF and, at 10° C., 2.1 eq. of KOtBu (1.5 g) were added, and the mixture was stirred for about 20 min. Then, at RT 2.5 g of ethyl bromopropionate were added dropwise and, after stirring at RT for 1 h, further KOtBu (0.2 g) and ethyl bromopropionate (0.8 g) were added. After a further 2 h, the mixture was diluted with CH2Cl2, washed with H2O, dried and concentrated. Chromatography on silica gel (CH2Cl2CH3OH 1 to 25%) afforded 1.2 g of the required product and 2.0 g of nonreacted precursor.

Workup

  1. stirringafter stirring at RT for 1 h
  2. waitAfter a further 2 h
  3. washwashed with H2O
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1fea0fe1bcbb4ee5b75e2b0b8fd1c342
Source dataset
uspto-grants-2006_09
Patent number
US07105508B1

Reaction notes

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