Lithium iodide → (S)-3-[4-(Benzyloxy)-2-fluorophenyl]-2-(Fmoc-amino)propanoic Acid

HRID 707500Notes

Reaction equation

HRID 707500 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([NH:21][C:22]([O:24][CH2:25][CH:26]2[C:38]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[C:32]3[C:27]2=[CH:28][CH:29]=[CH:30][CH:31]=3)=[O:23])[C:17]([O:19]C)=[O:18])=[C:11]([F:39])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-].[Li+]>C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([NH:21][C:22]([O:24][CH2:25][CH:26]2[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:32]=3[C:33]3[C:38]2=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:23])[C:17]([OH:19])=[O:18])=[C:11]([F:39])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 118162421Methyl (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-(benzyloxy)-2-fluorophenyl)propanoate

Product 1

HCID 118162511(S)-3-[4-(Benzyloxy)-2-fluorophenyl]-2-(Fmoc-amino)propanoic AcidYield 72.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a mixed solution of methyl(2S)-3-(4-(benzyloxy)-2-fluorophenyl)-2-(((9H-fluoren-9-ylmethoxy)carbonyl)amino)propanoate (60.0 g, 114 mmol) described in Production Example 1-2-6 and ethyl acetate (1331 mL) was added lithium iodide (92.0 g, 685 mmol) at room temperature. The resultant mixture was stirred under reflux for 23 hours and 45 minutes. The reaction mixture was cooled to 0° C., and a precipitate was collected by filtration. To the resultant solid was added 1 N hydrochloric acid (228 mL). The resultant solution was extracted with ethyl acetate. An organic layer was dried over anhydrous magnesium sulfate and then filtrated. The solvent was evaporated under a reduced pressure to give the title compound (42.2 g, yield: 72%).

Workup

  1. temperatureunder reflux for 23 hours and 45 minutes
  2. filtrationa precipitate was collected by filtration
  3. additionTo the resultant solid was added 1 N hydrochloric acid (228 mL)
  4. extractionThe resultant solution was extracted with ethyl acetate
  5. dry with materialAn organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltrated
  7. customThe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-c5da9bf3af0240d7998f1987dc873dbc
Source dataset
uspto-grants-2015_11
Patent number
US09174998B2

Reaction notes

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