Formaldehyde → HCID 53851245, compound

HRID 1789932Notes

Reaction equation

HRID 1789932 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH:5]([CH2:9][C:10]1[S:14][C:13]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[N:12][CH:11]=1)[C:6](O)=O)[CH3:2].C=O.C(Cl)Cl.C(NCC)C>O>[CH2:1]([O:3][C:4](=[O:23])[C:5]([CH2:9][C:10]1[S:14][C:13]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[N:12][CH:11]=1)=[CH2:6])[CH3:2]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6344DichloromethaneHCID 8021DiethylamineHCID 86760124HCID 86760124, compound

Product 1

HCID 53851245HCID 53851245, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-(2-tert- butoxycarbonylamino-thiazol-5-ylmethyl)-malonic acid monoethyl ester (94 mg; 0.27 mmol), a 36% aqueous solution of formaldehyde (36 μl; 1.2 mmol), CH2Cl2 (0.2 mL) and water (0.2 mL) was added at 0° C. diethyl amine (30 μl; 0.40 mmol). The reaction mixture was stirred at room temperature overnight, poured onto ice-water and extracted with CH2Cl2. The combined organic phases were washed with 5% NaHCO3, dried and concentrated to yield 2-(2-tert-butoxycarbonylamino-thiazol-5-ylmethyl)-acrylic acid ethyl ester (69 mg, 80.9%).

Workup

  1. additionpoured onto ice-water
  2. extractionextracted with CH2Cl2
  3. washThe combined organic phases were washed with 5% NaHCO3
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4a82f4f0a3034c1299a779581fcf48d0
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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