Lithium hydroxide, monohydrate → HCID 54173651, compound

HRID 1729101Notes

Reaction equation

HRID 1729101 reaction equation
[CH3:1][C:2]([C:32]([O:34]C)=[O:33])([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:20][CH:19]=1)[NH:3][C:4]([O:6][CH:7]1[CH:14]2[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:16][CH:8]1[CH2:9]3)[CH2:13]2)=[O:5].O.[OH-].[Li+]>O1CCOCC1.O>[CH3:1][C:2]([C:32]([OH:34])=[O:33])([CH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:22][CH:23]=1)[NH:3][C:4]([O:6][CH:7]1[CH:8]2[CH2:9][CH:10]3[CH2:11][CH:12]([CH2:13][CH:14]1[CH2:15]3)[CH2:16]2)=[O:5]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 53645933HCID 53645933, compound

Product 1

HCID 54173651HCID 54173651, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of methyl α-methyl-O-(phenylmethyl)-N-[(tricyclo[3.3.1.13,7 ]dec-2-yloxy)-carbonyl]-DL-tyrosinate (1.10 g, 0.0023 mol) in 8.8 mL dioxane and 4.4 mL water, lithium hydroxide monohydrate (0.145 g, 0.003 mmol, 1.5 eq) was added. This reaction mixture was then stirred for 48 hours at room temperature. The reaction mixture was then concentrated in vacuo and the resulting white syrup was diluted with 20 mL H2O. Thisbasic solution (pH 13) was then acidified (pH 2) with 1 mL 10% HCl, upon which white solid precipitated. This acidified aqueous suspension was thenextracted three times each with ether. The combined organic layers were dried (Na2SO4) and concentrated in vacuo to give the desired product (0.78 g, 0.0016 mmol, 73%). MS: 464.3 (MH+); 463.3 (M+).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. additionthe resulting white syrup was diluted with 20 mL H2O
  3. customupon which white solid precipitated
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-01123e0360ef41f1ab035547dd170146
Source dataset
uspto-grants-1994_07
Patent number
US05331006

Reaction notes

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