Methanol → HCID 59164851, compound

HRID 2264797Notes

Reaction equation

HRID 2264797 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]3[NH:19][C@H:18]([C:20]([O:22]C)=[O:21])[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO>C1COCC1.O>[C:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]3[NH:19][C@H:18]([C:20]([OH:22])=[O:21])[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 59164839HCID 59164839, compound

Product 1

HCID 59164851HCID 59164851, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl (5R)-5-{4-[(phenylmethyl)oxy]phenyl}-L-prolinate (D8, 120 mg, 0.38 mmol) in THF (2.3 ml) was added LiOH monohydrate (26 mg, 0.61 mmol) dissolved in water (1.1 ml) followed by methanol (1.1 ml). The resulting solution was stirred at room temperature for 3 hours (hydrolysis being monitored by HPLC). When hydrolysis was complete, the organic solvent was evaporated under reduced pressure (maintaining the temperature at 38° C.) to give a crude aqueous residue containing the title compound; Rt (HPLC)=3.63 min; MS: (ES/+) m/z: 298 [MH+], C18H19NO3 requires 297).

Workup

  1. custom(hydrolysis being monitored by HPLC)
  2. customWhen hydrolysis
  3. customthe organic solvent was evaporated under reduced pressure (
  4. temperaturemaintaining the temperature at 38° C.)
  5. customto give a crude aqueous residue

Sources & evidence

ORD record
ord-04d3dbd1efff4c4e9d4062f98759563b
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

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