Sodium Carbonate → HCID 145857605, compound

HRID 723150Notes

Reaction equation

HRID 723150 reaction equation
C(OC([N:8]1[C:12]2[CH:13]=[C:14]([S:18]([C:21]3[CH:25]=[C:24]([C:26]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[NH:27])[S:23][C:22]=3[S:36][CH3:37])(=[O:20])=[O:19])[CH:15]=[C:16]([Br:17])[C:11]=2[N:10]=[CH:9]1)=O)(C)(C)C.C([O-])([O-])=O.[Na+].[Na+]>CO>[C:32]([O:31][C:29](=[O:30])[NH:28][C:26]([C:24]1[S:23][C:22]([S:36][CH3:37])=[C:21]([S:18]([C:14]2[CH:15]=[C:16]([Br:17])[C:11]3[N:10]=[CH:9][NH:8][C:12]=3[CH:13]=2)(=[O:19])=[O:20])[CH:25]=1)=[NH:27])([CH3:35])([CH3:34])[CH3:33]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 145857716HCID 145857716, compound

Product 1

HCID 145857605HCID 145857605, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-bromo-6-[5-(tert-butoxycarbonylamino-imino-methyl)-2-methylsulfanyl-thiophene-3-sulfonyl]-benzoimidazole-1-carboxylic acid tert-butyl ester ((from above step b) 1.00 g, 1.58 mmol) in MeOH (10 mL) was treated with aqueous Na2CO3 (0.340 g, 3.17 mmol in 2 mL water). The reaction mixture was stirred at room temperature 30 min., and solvents were removed in vacuo. The residue was taken up in EtOAc and washed with water (1×50 mL) and brine (1×50 mL). The organic layer was dried over MgSO4 and concentrated in vacuo to afford the product {[4-(7-bromo-3H-benzoimidazole-5-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (0.755 g, 90%) as a brown solid. 1H NMR (MeOD): δ 8.48 (s, 1H), 8.32 (m, 1H), 8.20 (s, 1H), 8.03 (d, 1H, J=1.6 Hz), 2.63 (s, 3H), 1.48 (s, 9H).

Workup

  1. customsolvents were removed in vacuo
  2. washwashed with water (1×50 mL) and brine (1×50 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2af4323ccd494a419d7a913efcb85b23
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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