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ChemicalBook CAS DataBase List METHYL (3R)-3-AMINO-3-(4-CHLOROPHENYL)PROPANOATE

METHYL (3R)-3-AMINO-3-(4-CHLOROPHENYL)PROPANOATE synthesis

1synthesis methods
methyl 3-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoate

1143534-42-2
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METHYL (3R)-3-AMINO-3-(4-CHLOROPHENYL)PROPANOATE

283159-92-2
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Yield:283159-92-2 98%

Reaction Conditions:

with hydrogenchloride in 1,4-dioxane;dichloromethane at 20; for 3 h;

Steps:



Intermediate 40: (R)-methyl 3-amino-3-(4-chlorophenyl)propanoate (hydrochloride)Hydrochloric acid (4.0M in dioxane) (7.89 mL, 31.55 mmol) was added in one portion to (R)-methyl 3-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoate (Intermediate 39) (990 mg, 3.16 mmol) in DCM (20 mL) at 2O0C. The resulting solution was stirred at 20 0C for 3 hours. The reaction mixture was evaporated to afford (R)-methyl 3-amino-3-(4-chlorophenyl)propanoate (hydrochloride) (777 mg, 98 %) as a yellow solid. 1U NMR (399.9 MHz, DMSO-d6) δ 2.99 - 3.05 (IH, m), 3.18 - 3.23 (IH, m), 3.58 (3H, d), 4.62 - 4.65 (IH, m), 7.49 - 7.53 (2H, m), 7.57 - 7.61 (2H, m), 8.72 (3H, s). MS m/e MH+ 214; HPLC tR = 1.71 min.

References:

WO2009/47563,2009,A1 Location in patent:Page/Page column 111

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