Hydrochloric Acid → (3R)-1-(((cyclohexyloxy)carbonyl)oxy)ethyl 3-amino-4-(5'-chloro-2'-fluoro-[1,1'-biphenyl]-4-yl)butanoate

HRID 1752941Notes

Reaction equation

C(OC([NH:8][C@H:9]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:34]=2[F:40])=[CH:29][CH:28]=1)[CH2:10][C:11]([O:13][CH:14]([O:16][C:17]([O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:18])[CH3:15])=[O:12])=O)(C)(C)C.Cl>O1CCOCC1>[NH2:8][C@H:9]([CH2:26][C:27]1[CH:28]=[CH:29][C:30]([C:33]2[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:34]=2[F:40])=[CH:31][CH:32]=1)[CH2:10][C:11]([O:13][CH:14]([O:16][C:17]([O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:18])[CH3:15])=[O:12]

Participants

Conditions

Temperature: 23 °C

Procedure

To (3R)-1-(((cyclohexyloxy)carbonyl)oxy)ethyl 3-((tert-butoxycarbonyl)amino)-4-(5′-chloro-2′-fluoro-[1,1′-biphenyl]-4-yl)butanoate (2.02 g, 3.49 mmol) was added 9 mL of 4M HCl in 1,4-dioxane. The reaction mixture was stirred at 23° C. for approximately 1 hour. The reaction mixture was evaporated approximately to dryness to afford (3R)-1-(((cyclohexyloxy)carbonyl)oxy)ethyl 3-amino-4-(5′-chloro-2′-fluoro-[1,1′-biphenyl]-4-yl)butanoate (approximately 1.73 g, 104%) and taken directly to the next step. LCMS (ES+) C25H29ClFNO5: Calc.: 477.2; Found: 478.2[M+H]+.

Workup

customThe reaction mixture was evaporated approximately to dryness

Sources & evidence

ORD record: ord-bd8d39f79a344c59ba21a6e3ef51d668
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163040B2

Reaction notes

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