Phosphoric Acid → HCID 86746933, compound

HRID 1587599Notes

Reaction equation

HRID 1587599 reaction equation
[C:1]1([CH3:11])[CH:6]=CC(S(O)(=O)=O)=C[CH:2]=1.CO[C:14](OC)([CH3:16])[CH3:15].CC(C)(OC(N[C@H]([C:31]([NH:33][CH:34]([CH2:43][CH:44]1[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]1)[CH:35]([P:37]([O:41][CH3:42])([O:39][CH3:40])=[O:38])[OH:36])=[O:32])CC(C)C)=O)C.CC1C=CC=CC=1.[OH:58]P(O)(O)=O>C1C=CC=CC=1.CO>[CH:44]1([CH2:43][C@H:34]2[CH:35]([P:37]([O:39][CH3:40])([O:41][CH3:42])=[O:38])[O:36][C:14]([CH3:16])([CH3:15])[N:33]2[C:31]([O:32][C:1]([CH3:11])([CH3:6])[CH3:2])=[O:58])[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49]1

Participants

8

Reactant 5

HCID 1004Phosphoric AcidHCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 64952,2-Dimethoxypropane2×HCID 86746934HCID 86746934, compound

Product 1

HCID 86746933HCID 86746933, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent3×HCID 887MethanolSolvent

Procedure

p-Toluenesulfonic acid (28.5 mg, 0.15 mmol) and 2,2-dimethoxypropane (3.075 ml, 25 mmol) were added to a solution of compound D from Example 1 (3.65 g, 10 mmol) in 30 ml benzene. The solution was refluxed for 30 minutes after which benzene was slowly distilled over a period of 1 hour by which time the volume in the reaction flask had reduced to 10 ml. Fresh portions of p-toluene solfonic acid (28.5 mg, 0.15 mmol), 2,2-dimethoxypropane (6.16 ml, 50 mmol) and benzene (25 ml) and the slow distillation was repeated. The addition and distillation sequence was repeated five more times after which the reaction was judged almost complete by TLC. The reaction mixture was concentrated and the residue (4.5 g) chromatographed (150 g silica gel, 1:1 hexane/ethyl acetate to 2:8:0.1 hexane/ethyl acetate/acetic acid) to yield 3.524 g (87%) pure title A compound and 0.314 g (8.6%) of unreacted starting material, [α]D =-5.8° (c=0.89 CH3OH) which was characterized by MS, 1H NMR, 13C NMR and 31P NMR [23.3 and 20.2 ppm 9:1) w.r.t. H3PO4 =0, external standard 36.5 MHz].

Workup

  1. distillationwas slowly distilled over a period of 1 hour by which time the volume in the reaction flask
  2. additionThe addition and distillation sequence
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue (4.5 g) chromatographed (150 g silica gel, 1:1 hexane/ethyl acetate to 2:8:0.1 hexane/ethyl acetate/acetic acid)
  5. customto yield 3.524 g (87%) pure title A compound and 0.314 g (8.6%)
  6. customr.t

Sources & evidence

ORD record
ord-ef09700bab4b4a66be1c1c456a7bcc21
Source dataset
uspto-grants-1993_06
Patent number
US05217958

Reaction notes

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