Water → HCID 59496620, compound

HRID 449440Notes

Reaction equation

HRID 449440 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[NH2:6][CH:7]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[CH2:8][C:9]([OH:11])=[O:10].C(=O)([O-])[O-].[K+].[K+].O.O1CCCC1>>[CH:12]1([CH:7]([NH:6][C:2]([O:4][CH3:5])=[O:3])[CH2:8][C:9]([OH:11])=[O:10])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

6

Reactant 5

HCID 962WaterHCID 6586Methyl chloroformateHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 27336813-Amino-3-cyclohexylpropanoic acid

Product 1

HCID 59496620HCID 59496620, compoundYield 97.1%

Procedure

Methyl chloroformate (54 uL, 0.70 mmol) was added to a mixture of 3-amino-3-cyclohexylpropanoic acid (100.0 mg, 0.5840 mmol) (Key Organics/Bionet, Cat. #7T-0112) and potassium carbonate (160 mg, 1.2 mmol) in water (2.0 mL, 110 mmol) and tetrahydrofuran (2.0 mL, 25 mmol). After stirring at r.t. for 10 min, the mixture was extracted with ether to remove impurity. The aqueous layer was adjusted to pH=2 with HCl, and extracted with ethyl acetate (3×10 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure to afford the desired product (130 mg, 97%). Analytic LCMS (M+H)+: m/z=230.1.

Workup

  1. extractionthe mixture was extracted with ether
  2. customto remove impurity
  3. extractionextracted with ethyl acetate (3×10 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bc634a5758574bf798c8210d5c416cda
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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