Hydrochloric Acid → HCID 53715070, compound

HRID 1789816Notes

Reaction equation

HRID 1789816 reaction equation
ClC(OC)=O.[CH2:6]([O:8][C:9](=[O:31])[C:10]([CH2:16][C:17]1[CH:18]=[N:19][C:20]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:21][CH:22]=1)([CH2:14][CH3:15])[C:11](O)=[O:12])[CH3:7].CCN(CC)CC.[BH4-].[Na+].Cl>C1COCC1.C(Cl)Cl>[CH2:6]([O:8][C:9](=[O:31])[C:10]([CH2:16][C:17]1[CH:18]=[N:19][C:20]([NH:23][C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])=[CH:21][CH:22]=1)([CH2:11][OH:12])[CH2:14][CH3:15])[CH3:7]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 54026915HCID 54026915, compound

Product 1

HCID 53715070HCID 53715070, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl chloroformate (150 pL, 1.95 mmol) was added dropwise to a solution of 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-2-ethyl-malonic acid monoethyl ester (700 mg, 1.91 mmol) and Et3N (275 μL, 1.97 mmol) in THF (15 mL) at −20° C. under nitrogen. The reaction mixture was stirred for 50 min., filtered and added dropwise to a suspension of NaBH4 (80 mg, 2.1 mmol) in THF (15 mL) at −20° C. The reaction was stirred for 16 h at room temperature. 0.2 M HCl was added followed by methylene chloride. The organic phase was washed with brine and dried. Concentration under reduced pressure followed by chromathography (toluene/EtOAc, 3:1→1:3) gave 2-(6-tert-butoxycarbonylamino pyridin-3-ylmethyl)-2-hydroxymethyl-butyric acid ethyl ester (300 mg, 45%).

Workup

  1. filtrationfiltered
  2. stirringThe reaction was stirred for 16 h at room temperature
  3. washThe organic phase was washed with brine
  4. customdried
  5. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-eecf4b8b12244c0d82a0c50d09c6c711
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

Loading…