Bicarbonate Ion → (2-Amino-thiazol-5-yl)-propynoic acid ethyl ester

HRID 1889182Notes

Reaction equation

HRID 1889182 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]#[C:6][C:7]1[S:11][C:10]([NH:12]C(OC(C)(C)C)=O)=[N:9][CH:8]=1)[CH3:2].FC(F)(F)C(O)=O.C(=O)(O)[O-]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:20])[C:5]#[C:6][C:7]1[S:11][C:10]([NH2:12])=[N:9][CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 769Bicarbonate IonHCID 6422Trifluoroacetic acid2×HCID 59610061(2-Tert-butoxycarbonylamino-thiazol-5-yl)-propynoic acid ethyl ester

Product 1

HCID 59610026(2-Amino-thiazol-5-yl)-propynoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2-tert-Butoxycarbonylamino-thiazol-5-yl)-propynoic acid ethyl ester (1.2 g, 4.049 mmol) was dissolved in DCM (20 ml), trifluoroacetic acid (4.617 g, 40.93 mmol) was added in drop wise fashion at 0° C. After complete addition the reaction was allowed to stir for overnight at room temperature. Additional 3 ml of TFA was charged to the reaction and stirred for 2 hr. TLC showed complete reaction. Reaction was basified with sat. bicarbonate. The aqueous layer was extracted with ethyl acetate (30 ml×3). The combined organic layer was washed with water followed by brine and dried over anhydrous sodium sulfate and the solvent was removed on vacuo. The sticky solid product was obtained (0.700 g)

Workup

  1. additionAfter complete addition the reaction
  2. stirringstirred for 2 hr
  3. customreaction
  4. customReaction
  5. extractionThe aqueous layer was extracted with ethyl acetate (30 ml×3)
  6. washThe combined organic layer was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was removed on vacuo
  9. customThe sticky solid product was obtained (0.700 g)

Sources & evidence

ORD record
ord-8d2d2c20bd6b45f4919e12247acbfbe3
Source dataset
uspto-grants-2013_08
Patent number
US08501955B2

Reaction notes

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