Hydrochloric Acid → (R)-benzyl 3-amino-4-(3'-chlorobiphenyl-4-yl)butanoate hydrochloride

HRID 70879Notes

Reaction equation

HRID 70879 reaction equation
C(OC([NH:8][C@H:9]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=2)=[CH:24][CH:23]=1)[CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=O)(C)(C)C.Cl.O1CCOCC1>>[ClH:34].[NH2:8][C@H:9]([CH2:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=2)=[CH:26][CH:27]=1)[CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59607651(R)-benzyl 3-(tert-butoxycarbonylamino)-4-(3'-chlorobiphenyl-4-yl)butanoate

Product 1

HCID 86648193(R)-benzyl 3-amino-4-(3'-chlorobiphenyl-4-yl)butanoate hydrochlorideYield 201.3%

Procedure

To (R)-benzyl 3-(tert-butoxycarbonylamino)-4-(3′-chlorobiphenyl-4-yl)butanoate (3.561 g, 7.42 mmol) is added a solution of 4 M HCl in 1,4-dioxane (18.55 mL, 74.2 mmol) at room temperature. After stirring for 4 hours, the reaction mixture is concentrated under reduced pressure to give (R)-benzyl 3-amino-4-(3′-chlorobiphenyl-4-yl)butanoate hydrochloride (3.11 g). HPLC retention time=1.07 minutes (condition B); MS (m+1)=380.1; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.81 (A of ABX, Jab=17.4 Hz, Jax=4.5 Hz, 1 H) 2.93 (B of ABX, Jab=17.4 Hz, Jbx=7.6 Hz, 1 H) 3.03-3.09 (m, 1 H) 3.50 (dd, J=4.9 and 13.5 Hz, 1 H) 3.98 (br s, 1 H) 5.09 (s, 2 H) 7.24-7.22 (m, 9 H) 7.35-7.38 (m, 1 H) 7.42 (d, J=8.1 Hz, 2 H) 7.48-7.49 (m, 1 H) 8.78 (br s, 3 H).

Workup

  1. concentrationthe reaction mixture is concentrated under reduced pressure

Sources & evidence

ORD record
ord-cb0106b2d2be48be9a39b8b4d375ba55
Source dataset
uspto-grants-2014_09
Patent number
US08822534B2

Reaction notes

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