Hydrochloric Acid → HCID 178523388, compound

HRID 1434479Notes

Reaction equation

HRID 1434479 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](ON3C(=O)CCC3=O)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[NH2:26][CH2:27][C@H:28]1[CH2:33][CH2:32][C@H:31]([C:34]([OH:36])=[O:35])[CH2:30][CH2:29]1.Cl>O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+]>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:26][CH2:27][C@H:28]3[CH2:29][CH2:30][C@H:31]([C:34]([OH:36])=[O:35])[CH2:32][CH2:33]3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 178511262HCID 178511262, compound

Product 1

HCID 178523388HCID 178523388, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of N-(9-fluorenylmethoxycarbonyloxy)succinimide (4.4 g; 14.0 mmol) in 1,4-dioxane (40 mL) was added dropwise to a solution of trans-4-(aminomethyl)cyclohexanecarboxylic acid (2.0 g; 12.7 mmol) in 10% Na2CO3 (30 mL) cooled to 0° C. The mixture was then allowed to warm to ambient temperature and after 1 h stirring at room temperature was treated with 1 N HCl (32 mL) until the final pH was 2. The resulting solution was extracted with n-BuOH (100 mL); the volatiles were removed and the crude residue was purified by flash chromatography to give D as a white solid (1.6 g; 4.2 mmol). Yield 33%.

Workup

  1. temperatureto warm to ambient temperature and after 1 h
  2. extractionThe resulting solution was extracted with n-BuOH (100 mL)
  3. customthe volatiles were removed
  4. customthe crude residue was purified by flash chromatography
  5. customto give D as a white solid (1.6 g; 4.2 mmol)

Sources & evidence

ORD record
ord-6ec295e003ef48029227a4d5f67c2153
Source dataset
uspto-grants-2009_11
Patent number
US07611692B2

Reaction notes

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