Citric Acid → HCID 67460002, compound

HRID 625068Notes

Reaction equation

HRID 625068 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([C:12]2([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:14][CH2:13]2)[CH:10]=[O:11])=[CH:4][CH:3]=1.CC(=CC)C.[OH:28]P([O-])(O)=O.[K+].Cl([O-])=O.[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CC(O)(C)C.O>[C:18]([O:17][C:16]([NH:15][C:12]1([CH:9]([CH2:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:10]([OH:28])=[O:11])[CH2:14][CH2:13]1)=[O:22])([CH3:19])([CH3:21])[CH3:20]

Participants

8

Reactant 5

HCID 311Citric AcidHCID 105532-Methyl-2-buteneHCID 516951Monobasic potassium phosphateHCID 23668197Sodium ChloriteHCID 86675330HCID 86675330, compound

Product 1

HCID 67460002HCID 67460002, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

tert-Butyl 1-(1-(4-chlorophenyl)-3-oxopropan-2-yl)cyclopropylcarbamate (3.06 mmol), 2-methyl-2-butene (7.6 mL, 2.0M THF solution, 15.3 mmol) and KH2PO4 (0.416 g, 3.06 mmol) were dissolved in t-BuOH (100 mL)-water (30 mL). Sodium chlorite (0.830 g, 9.17 mmol) was added portionwise at 0° C. The mixture was stirred at room temperature for 2 hours and then acidified with 10% citric acid. The reaction was extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated to give 2-(1-(tert-butoxycarbonylamino)cyclopropyl)-3-(4-chlorophenyl)propanoic acid as a white solid. LCMS: 339.9 [M+H+] (APCI+).

Workup

  1. extractionThe reaction was extracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-281351a6f2db4fcb948a9c53a9b32201
Source dataset
uspto-grants-2016_04
Patent number
US09303040B2

Reaction notes

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