1-Propene, 1-methoxy- → HCID 12186155, compound

HRID 499700Notes

Reaction equation

HRID 499700 reaction equation
[CH2:1]([O:8][C:9](=[O:23])[CH2:10][CH2:11][C@H:12]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13][OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[C:25]1(C)[CH:30]=CC(S(O)(=O)=O)=C[CH:26]=1.COC=CC>C(Cl)Cl>[C:19]([O:18][C:16]([N:15]1[C@@H:12]([CH2:11][CH2:10][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:23])[CH2:13][O:14][C:25]1([CH3:30])[CH3:26])=[O:17])([CH3:20])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 1112901-Propene, 1-methoxy-HCID 521998p-Toluenesulfonic acid monohydrateHCID 11198087HCID 11198087, compound

Product 1

HCID 12186155HCID 12186155, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 52.46 g of 4(S)-tert-butoxycarbonylamino-5-hydroxy-pentanoic acid benzyl ester [9069-62-8] and 895 mg of p-toluenesulfonic acid hydrate in 125 ml of methylene chloride at 0° C. under argon are added 31 ml of methoxypropene over 15 minutes. The mixture is stirred at 0° C. for 3 hours, then at room temperature for 9 hours. The mixture is washed with saturated sodium bicarbonate solution and dried over sodium sulphate, filtered and concentrated. The title compound is obtained as a yellow oil from the residue by means of flash chromatography (SiO2 60 F). Rf=0.32 (1:3 EtOAc-heptane); Rt=5.32 (gradient I).

Workup

  1. waitat room temperature for 9 hours
  2. washThe mixture is washed with saturated sodium bicarbonate solution
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c86306703f284f3480d3cff5851b04ce
Source dataset
uspto-grants-2010_08
Patent number
US07767690B2

Reaction notes

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