Water → HCID 178418468, compound

HRID 1695

Reaction equation

HRID 1695 reaction equation
[C:1]([NH:8][C@H:9]1[CH2:14][CH2:13][C@@H:12]([C:15]([O:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=[O:23])=[C:20]([O:28][CH3:29])[CH:19]=2)=[O:16])[CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O.O[Li].O>C1COCC1>[C:1]([NH:8][C@H:9]1[CH2:14][CH2:13][C@@H:12]([C:15]([O:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([OH:24])=[O:23])=[C:20]([O:28][CH3:29])[CH:19]=2)=[O:16])[CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 178418455HCID 178418455, compound

Product 1

HCID 178418468HCID 178418468, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a stirred solution of methyl 4-[N-Boc-cis-1-amino-4-cyclohexanoyloxy]-2-methoxybenzoate (220 mg, 0.52 mmol) in THF:H2O (5 mL: 1 mL) was added LiOH.H2O (67.6 mg, 1.59 mmol). The reaction was heated to 45° C. over 12 h and then cooled to ambient temperature. The solvent was removed under reduced pressure. The crude solid passed through a plug of silca gel packed in 50:50 MeOH:CH2Cl2 and eluted with same. The solvent was removed under reduced pressure to afford 4-[N-Boc-cis-1-amino-4-cyclohexanoyloxy]-2-methoxybenzoic acid as a white solid.

Workup

  1. temperaturecooled to ambient temperature
  2. customThe solvent was removed under reduced pressure
  3. washCH2Cl2 and eluted with same
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c883c9ea34ed4863b03fce02c544723e
Source dataset
uspto-grants-1998_03
Patent number
US05726172

Linked notes

Loading…