Dichloromethane → HCID 86595065, compound
Reaction equation
FC(F)(F)C(O)=O.C([O:10][C:11](=[O:40])[C@@H:12]([O:37][CH2:38][CH3:39])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([NH:29]C(OC(C)(C)C)=O)=[CH:25][CH:24]=2)=[CH:16][CH:15]=1)C.[Cl:41]CCl>>[ClH:41].[NH2:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][CH2:21][O:20][C:17]2[CH:18]=[CH:19][C:14]([CH2:13][C@H:12]([O:37][CH2:38][CH3:39])[C:11]([OH:40])=[O:10])=[CH:15][CH:16]=2)=[CH:28][CH:27]=1Participants
Procedure
Trifluoroacetic acid (12 ml; 0.0706 mole) was added to a solution of 3-{4-[2-(4-tert-butoxycarbonylaminophenyl)ethoxy]phenyl}-(S)-2-ethoxypropanoic acid ethyl ester (30 g; 0.065 mole) in dichloromethane (150 ml). The reaction mixture was stirred over night at room temperature and then washed three times with water. The organic phase was dried with magnesium sulfate and evaporated. 1H-NMR of the product showed a mixture of product and starting material. The crude product (27.3 g) was redissolved in ethyl acetate, ethyl acetate saturated with hydrochloric acid (500 ml) was added and the mixture was stirred over night at room temperature. Evaporation gave 24.7 g (96.5% yield) of 3-{4-[2-(4-aminophenyl)ethoxy]phenyl}-(S)-2-ethoxypropanoic acid hydro chloride.
Workup
- washwashed three times with water
- dry with materialThe organic phase was dried with magnesium sulfate
- customevaporated
- additiona mixture of product
- dissolutionThe crude product (27.3 g) was redissolved in ethyl acetate
- additionethyl acetate saturated with hydrochloric acid (500 ml) was added
- stirringthe mixture was stirred over night at room temperature
- customEvaporation
Sources & evidence
- ORD record
- ord-0afa3de3ded24d77b7b724fc7f0e29dc
- Source dataset
- uspto-grants-2003_10
- Patent number
- US06630600B1
Reaction notes
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