Hydrochloric Acid → HCID 118574942, compound

HRID 632707Notes

Reaction equation

HRID 632707 reaction equation
C(OC([NH:8][C@@H:9]([CH:47]([CH3:49])[CH3:48])[C:10]([O:12][C:13]1[CH:14]=[CH:15][C:16]2[C:20]([O:21][C:22]3[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/[C:30]([O:32]C(C)(C)C)=[O:31])=[CH:24][CH:23]=3)=[C:19]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[CH:43]([CH3:45])[CH3:44])[S:18][C:17]=2[CH:46]=1)=[O:11])=O)(C)(C)C.[ClH:50]>>[ClH:50].[NH2:8][C@@H:9]([CH:47]([CH3:49])[CH3:48])[C:10]([O:12][C:13]1[CH:14]=[CH:15][C:16]2[C:20]([O:21][C:22]3[CH:23]=[CH:24][C:25](/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31])=[CH:26][CH:27]=3)=[C:19]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[CH:43]([CH3:44])[CH3:45])[S:18][C:17]=2[CH:46]=1)=[O:11]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 118574959HCID 118574959, compound

Product 1

HCID 118574942HCID 118574942, compoundYield 85%

Procedure

A solution of (S,E)-3-(4-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)phenoxy)-2-(2-isopropylphenyl)benzo[b]thiophen-6-yl 2-((tert-butoxycarbonyl)amino)-3-methylbutanoate (106.8 mg, 0.156 mmol) in HCl (2.0 mL, 4N in 1,4-dioxane) was stirred at room temperature for 18 hours after which time the mixture was concentrated in vacuo to remove HCl and 1,4-dioxane. The resulting crude material was then triturated with heptane (2×) to obtain (S,E)-3-(4-((6-((2-amino-3-methylbutanoyl)oxy)-2-(2-isopropylphenyl)benzo[b]thiophen-3-yl)oxy)phenyl)acrylic acid hydrochloride (54.1 mg, 0.094 mmol, 85% yield). 1H NMR (400 MHz, CD3OD) δ ppm=7.81 (d, J=2.02 Hz, 1H), 7.42-7.62 (m, 4H), 7.25-7.42 (m, 3H), 7.09-7.26 (m, 2H), 6.86 (d, J=8.59 Hz, 2 H), 6.32 (d, J=15.66 Hz, 1 H), 4.29 (d, J=5.05 Hz, 1H), 3.18 (s, 1 H), 2.44-2.60 (m, 1 H), 1.12-1.35 (m, 12H) HRMS (m/z, MH+): 530.1988.

Workup

  1. concentrationwas concentrated in vacuo
  2. customto remove HCl and 1,4-dioxane
  3. customThe resulting crude material was then triturated with heptane (2×)

Sources & evidence

ORD record
ord-0f46757b99a54716872ba2ca6167a9a4
Source dataset
uspto-grants-2016_04
Patent number
US09321746B2

Reaction notes

Loading…