Ethyl bromoacetate → HCID 68546571, compound

HRID 2243497Notes

Reaction equation

HRID 2243497 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[C:11]([C:14]([O:16][CH2:17][CH:18]=[CH2:19])=[O:15])[CH:12]=[CH:13][C:7]=2[C:6]=1[S:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[O:4].[CH2:26]1[CH2:36][CH2:35][N:34]2[C:29](=NCCC2)[CH2:28][CH2:27]1.Br[CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40].C([O-])([O-])=O.[K+].[K+].[NH4+].[Cl-]>CN(C=O)C.O>[C:39]([CH2:1][O:2][C:3]1[C:5]2[S:9][C:8]3[CH:10]=[C:11]([NH:34][CH:29]4[CH2:28][CH2:27][CH2:26][CH2:36][CH2:35]4)[CH:12]=[CH:13][C:7]=3[C:6]=2[S:20][C:21]=1[C:22]([OH:24])=[O:23])([OH:41])=[O:40].[CH3:25][O:24][C:22]([C:21]1[S:20][C:6]2[C:7]3[CH:13]=[CH:12][C:11]([C:14]([O:16][CH2:17][CH:18]=[CH2:19])=[O:15])=[CH:10][C:8]=3[S:9][C:5]=2[C:3]=1[O:4][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])=[O:23]

Participants

9

Reactant 5

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 68548906HCID 68548906, compound

Product 2

HCID 11718381HCID 11718381, compoundHCID 68546571HCID 68546571, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-methoxycarbonylmethylsulfanyl-benzo[b]thiophene-2,6-dicarboxylic acid 6-allyl ester 2-methyl ester (1.05 g, 2.76 mmol) in DMF was added DBU (0.83 mL, 5.53 mmoL) at room temperature. The resultant mixture was stirred for 24 hours. To this was added ethyl bromoacetate (0.92 mL, 8.28 mmoL) and K2CO3 (1.14 g, 8.26 mmoL). The reaction mixture was stirred for additional 2 hours, then aq. NH4Cl (200 mL and water (300 mL) was added. The white precipate was collected by filtration and washed with water to give the desired compound, 1-ethoxycarbonylmethoxy-3,8-dithia-cyclopenta[a]indene-2,6-dicarboxylic acid 6-allyl ester 2-methyl ester (1.162 g, 97% overall).

Workup

  1. filtrationThe white precipate was collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-ca74a27877714583b9a888ab2a34e133
Source dataset
uspto-grants-2010_03
Patent number
US07674822B2

Reaction notes

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