1,2-Dichloroethane → 2-Trityloxycarbamoyl-benzo[b]thiophene-5-carboxylic acid methyl ester

HRID 545474Notes

Reaction equation

HRID 545474 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:16]=[CH:15][C:8]2[S:9][C:10]([C:12]([OH:14])=O)=[CH:11][C:7]=2[CH:6]=1)=[O:4].[C:17]([O:36][NH2:37])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[CH:16]=[CH:15][C:8]2[S:9][C:10]([C:12](=[O:14])[NH:37][O:36][C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[CH:11][C:7]=2[CH:6]=1)=[O:4]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 3015602O-(triphenylmethyl)hydroxylamineHCID 595564095-(Methoxycarbonyl)benzo[b]thiophene-2-carboxylic acid

Product 1

HCID 866150442-Trityloxycarbamoyl-benzo[b]thiophene-5-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of benzo[b]thiophene-2,5-dicarboxylic acid 5-methyl ester (2.592 g, 10.97 mmol), O-trityl -hydroxylamine (3.020 g, 10.97 mmol), EDC (3.150 g, 16.48 mmol), HOBt (1.482 g, 10.97 mmol) and DIEA (4.80 mL, 27.6 mmol) in anhydrous THF (100 mL) was allowed to stir at rt for one week and then concentrated. To the residue was added MeOH (10 mL) and water (100 mL). The syrup obtained was washed with water (10 mL) and triturated with water (90 mL) to give 2-trityloxycarbamoyl-benzo[b]thiophene-5-carboxylic acid methyl ester as a pale solid. MS (EI): cal'd 243.1 (M-benzothiophene moiety+H+), exp 243.2 (M-benzothiophene moiety+H+).

Workup

  1. concentrationconcentrated
  2. additionTo the residue was added MeOH (10 mL) and water (100 mL)
  3. customThe syrup obtained
  4. washwas washed with water (10 mL)
  5. customtriturated with water (90 mL)

Sources & evidence

ORD record
ord-ca428f3e6b474114af183f0b7910d400
Source dataset
uspto-grants-2011_05
Patent number
US07935724B2

Reaction notes

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