Ethyl 2-((tert-butoxycarbonyl)amino)-4-(hydroxymethyl)thiophene-3-carboxylate → HCID 86596546, compound

HRID 1244156Notes

Reaction equation

HRID 1244156 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH2:11][OH:12])=[CH:9][S:8][C:7]=1[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:5])[CH3:2]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH:11]=[O:12])=[CH:9][S:8][C:7]=1[NH:13][C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 57354245Ethyl 2-((tert-butoxycarbonyl)amino)-4-(hydroxymethyl)thiophene-3-carboxylate

Product 1

HCID 86596546HCID 86596546, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

2-t-Butoxycarbonylamino-4-hydroxymethyl-thiophene-3-carboxylic acid ethyl ester (2.83 g, 9.44 mmol) was dissolved in anhydrous CH2Cl2 (165 mL) and treated with manganese dioxide (16.41 g, 188.70 mmol). It was stirred at room temperature for 5 hr then it was filtered through a pad of Celite. The Celite was washed with copious amounts of acetone. The filtrate was concentrated in vacuo to give title compound (2.69 g, 95%). MS m/e (CI) 300.0 (M+H)+; 1H NMR (300 MHz, CDCl3): δ ppm 1.42 (t, 3H), 1.55 (s, 9H), 4.43 (q, 2H), 7.59 (s, 1H), 10.30 (s, 1H), 10.34 (s, 1H).

Workup

  1. filtrationit was filtered through a pad of Celite
  2. washThe Celite was washed with copious amounts of acetone
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9dba245dee4646d4bc404fe3a40dee59
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

Loading…