Acetic Acid → HCID 19100734, compound

HRID 1974982Notes

Reaction equation

HRID 1974982 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:13]=1[C:14]([O:16]CC)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(N(C(OC(C)(C)C)=O)C1SC=C(CC(C)C)C=1C(OCC)=O)=O)(C)(C)C.[OH-].[K+].C(O)(=O)C>CO.O>[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:13]=1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 19100792HCID 19100792, compoundHCID 19100815HCID 19100815, compound

Product 1

HCID 19100734HCID 19100734, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of crude ethyl 2-t-butoxycarbonylamino-4-isobutylthiophene-3-carboxylate and ethyl 2-bis(t-butoxycarbonyl)amino-4-isobutylthiophene-3-carboxylate in methanol (1200 ml) was stirred and a solution of potassium hydroxide (44.8 g, 800 mmol) in water (450 ml) was added. The mixture was heated at 80° C. for 6h and left at room temperature over night. The reaction mixture was diluted with water and the pH adjusted to pH 4-5 with glacial acetic acid under cooling on ice. The product was extracted with ether and after drying with Na2SO4 the ether phase was concentrated in vacuo. The residue was suspended in petroleum ether and 2-t-butoxycarbonylamino-4-isobutylthiophene-3-carboxylic acid (75.2 g) was isolated by filtration. M.p. 154°-155° C. 1H-NMR (CDCl3, δ): 0.95 (d, 6H), 1.55 (s, 9H), 1.9 (m, 1H), 2.7 (d, 2H), 6.35 (s, 1H), 9.3 (br.s, 1H), 10.2 (s, 1H).

Workup

  1. waitleft at room temperature over night
  2. temperatureunder cooling on ice
  3. extractionThe product was extracted with ether
  4. dry with materialafter drying with Na2SO4 the ether phase
  5. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-6828dc1496974ff58342c252f27b88fe
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

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