Hydrochloric Acid → HCID 67439156, compound

HRID 1438130Notes

Reaction equation

HRID 1438130 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]([S:24]([CH:27]([CH3:29])[CH3:28])(=[O:26])=[O:25])=[C:6]([C@@H:8]2[C@@H:12]([C:13]([O:15][CH3:16])=[O:14])[CH2:11][CH2:10][N:9]2C(OC(C)(C)C)=O)[CH:7]=1.[Cl:30][C:31]([O:33][CH3:34])=[O:32].Cl>N1C=CC=CC=1>[ClH:30].[CH:27]([S:24]([C:5]1[CH:4]=[CH:3][C:2]([C:31]([O:33][CH3:34])=[O:32])=[CH:7][C:6]=1[C@H:8]1[C@@H:12]([C:13]([O:15][CH3:16])=[O:14])[CH2:11][CH2:10][NH:9]1)(=[O:25])=[O:26])([CH3:28])[CH3:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 69007853HCID 69007853, compound

Product 1

HCID 67439156HCID 67439156, compoundYield 129.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 61A (0.09 g, 0.21 mmol) in pyridine (1 mL) at 0° C. was added methyl chloroformate (32 μL, 0.42 mmol). After 2.0 h stirring at rt the reaction was acidified with 1M HCl to pH 3-4. The product was extracted with ethyl acetate and was washed with brine and dried over sodium sulfate. After evaporation of the solvent, the crude product was redissolved in ethyl acetate (1.5 mL) and hydrogen chloride (2 mL, 4M in dioxane) was added. The reaction was stirred for 3 h at rt. The solvent was removed and placed on the lyophilizer to give 0.11 g solid 61C. 1H NMR (400 MHz, Methanol-d4) δ ppm 1.22-1.40 (m, 6H) 2.43-2.60 (m, 1H) 2.62-2.80 (m, 1H) 3.42 (s, 3H) 3.45-3.65 (m, 2H) 3.67-3.77 (m, 1H) 3.78 (s, 3H) 3.83-3.96 (m, 1H) 5.84 (d, J=8.56 Hz, 1H) 7.55-7.67 (m, 1H) 7.81-7.90 (m, 1H) 7.94 (d, J=8.80 Hz, 1H).

Workup

  1. extractionThe product was extracted with ethyl acetate
  2. washwas washed with brine
  3. dry with materialdried over sodium sulfate
  4. customAfter evaporation of the solvent
  5. dissolutionthe crude product was redissolved in ethyl acetate (1.5 mL)
  6. additionhydrogen chloride (2 mL, 4M in dioxane) was added
  7. stirringThe reaction was stirred for 3 h at rt
  8. customThe solvent was removed

Sources & evidence

ORD record
ord-bc0d1a3dd1ff4dd69643cd528e8ad44a
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

Loading…