Tetrahydrofuran → HCID 67267869, compound

HRID 1696013Notes

Reaction equation

HRID 1696013 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH2:17][O:18][CH:19]([CH3:22])[CH2:20][Cl:21])[C:13]([O:15]C)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+].C1COCC1>C1COCC1.O>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH2:17][O:18][CH:19]([CH3:22])[CH2:20][Cl:21])[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 67268964HCID 67268964, compound

Product 1

HCID 67267869HCID 67267869, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of (R)-methyl 2-(benzyloxycarbonylamino)-3-(1-chloropropan-2-yloxy)propanoate (583 mg, 1.77 mmol) in THF—H2O (8 mL-4 mL) was added lithium hydroxide monohydrate (223 mg, 5.30 mmol). The mixture was stirred at room temperature for 25 minutes THF was removed in vacuo and the mixture extracted with EtOAc and dried over Na2SO4. Solvent was removed to give crude (R)-2-(benzyloxycarbonylamino)-3-(1-chloropropan-2-yloxy)propanoic acid as an oil. MS [M+H] found 316.2.

Workup

  1. customwas removed in vacuo
  2. extractionthe mixture extracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. customSolvent was removed

Sources & evidence

ORD record
ord-9c0da20aa44b4ac98e1f1dadb80359f9
Source dataset
uspto-grants-2012_04
Patent number
US08163755B2

Reaction notes

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