Triethylamine → Methyl 5-(tert-butoxycarbonylamino)-4-(2-methoxy-2-oxoethylamino)thiophene-2-carboxylate

HRID 1184897Notes

Reaction equation

HRID 1184897 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[S:5][C:6]=1[NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].C(N(CC)CC)C.Br[CH2:27][C:28]([O:30][CH3:31])=[O:29]>C(Cl)Cl>[C:11]([O:10][C:8]([NH:7][C:6]1[S:5][C:4]([C:15]([O:17][CH3:18])=[O:16])=[CH:3][C:2]=1[NH:1][CH2:27][C:28]([O:30][CH3:31])=[O:29])=[O:9])([CH3:12])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 60984Methyl bromoacetateHCID 67125667Methyl 4-amino-5-(tert-butoxycarbonylamino)thiophene-2-carboxylate

Product 1

HCID 67125563Methyl 5-(tert-butoxycarbonylamino)-4-(2-methoxy-2-oxoethylamino)thiophene-2-carboxylateYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-amino-5-(tert-butoxycarbonylamino)thiophene-2-carboxylate 89 (0.037 mmol, 10 mg) in CH2Cl2 (1 mL), triethylamine (0.367 mmol, 51.2 μL) and methyl bromoacetate (0.184 mmol, 17.45 μL) were added and stirred at rt for 3 h. The reaction was quenched in water and extracted with CH2Cl2. The organic layer was dried with phaseseparator whereafter and concentrated under reduced pressure to give methyl 5-(tert-butoxycarbonylamino)-4-(2-methoxy-2-oxoethylamino)thiophene-2-carboxylate 90 (10 mg, 79%). NMR (400 MHz, CDCl3) 1.54 (s, 9H), 3.31 (br s, 1H), 3.77 (s, 3H), 3.79 (d, J=6.3 Hz, 2H), 3.82 (s, 3H), 7.38 (s, 1H), 7.54 (br s, 1H). (m/z)=345 (M+H)+.

Workup

  1. customThe reaction was quenched in water
  2. extractionextracted with CH2Cl2
  3. customThe organic layer was dried with phaseseparator whereafter and
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-847eb4ca5f214f2db48e51b02b33158a
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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