Hydrochloric Acid → HCID 10977104, compound

HRID 850605Notes

Reaction equation

HRID 850605 reaction equation
[CH2:1]([O:3][C:4](=[O:39])[CH2:5][C@H:6]([NH:15]CCN(C(OC(C)(C)C)=O)CCCC1C=CC2CCCNC=2N=1)[C:7]1[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[N:11][CH:12]=1)[CH3:2].Cl.CO>CCOC(C)=O.C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:39])[CH2:5][C@@H:6]([C:7]1[CH:12]=[N:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)[NH2:15])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 11038835HCID 11038835, compound

Product 1

HCID 10977104HCID 10977104, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of the ester 7-6 (14.1 g, 26 mmol) in EtOAc (350 mL) cooled to -20° C. was treated with HCl (gas) for 10 minutes then stoppered and stirred at 0° C. for 1.5 hr. The volatiles were removed in vacuo, the residue taken up in 150 mL of water and treated with solid K2CO3 to pH~10. This solution was extracted with EtOAc (3×150 mL), washed with brine, dried (Na2SO4) and concentrated to give an oil. Column chromatography (silica gel; 5% MeOH in CHCl3) gave the β-alanine 7-5; further elution with 5% MeOH in CHCl3 saturated with NH3 gave 7-7 as a viscous oil. 1H NMR (300 MHz, CDCl3) δ 1.20 (3H, t), 1.8-1.95 (4H, m), 2.5-2.8 (12H, m), 3.39 (2H, m), 3.92 (3H, s), 4.09 (2H, q), 5.01 (1H, bs), 6.34 (1H, d), 6.72 (1H, d), 7.06 (1H, d), 7.59 (1H, dd), 8.07 (1H, d).

Workup

  1. customThe volatiles were removed in vacuo
  2. additiontreated with solid K2CO3 to pH~10
  3. extractionThis solution was extracted with EtOAc (3×150 mL)
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto give an oil

Sources & evidence

ORD record
ord-96635a3c443c4f359c24c44b75e96cc1
Source dataset
uspto-grants-2000_01
Patent number
US06017926

Reaction notes

Loading…