Phenylboronic Acid → (S,R)-{2-oxo-1-phenyl-2-[2-(2-phenyl-imidazo[2,1-b]thiazol-6-ylcarbamoyl)-pyrrolidin-1-yl]-ethyl}-carbamic acid tert-butyl ester

HRID 1811670Notes

Reaction equation

HRID 1811670 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][C@@H:8]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@@H:12]1[C:16](=[O:27])[NH:17][C:18]1[N:19]=[C:20]2[N:24]([CH:25]=1)[CH:23]=[C:22](Br)[S:21]2)=[O:10])([CH3:4])([CH3:3])[CH3:2].[C:35]1(B(O)O)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>>[C:1]([O:5][C:6](=[O:34])[NH:7][C@@H:8]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:9](=[O:10])[N:11]1[CH2:15][CH2:14][CH2:13][C@@H:12]1[C:16](=[O:27])[NH:17][C:18]1[N:19]=[C:20]2[N:24]([CH:25]=1)[CH:23]=[C:22]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[S:21]2)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 66827Phenylboronic AcidHCID 86654641(S,R)-{2-[2-(2-bromo-imidazo[2,1-b]thiazol-6-ylcarbamoyl)-pyrrolidin-1-yl]-2-oxo-1-phenyl-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 86654642(S,R)-{2-oxo-1-phenyl-2-[2-(2-phenyl-imidazo[2,1-b]thiazol-6-ylcarbamoyl)-pyrrolidin-1-yl]-ethyl}-carbamic acid tert-butyl esterYield 6%

Procedure

Compound A24 was synthesized from compound 12a (0.053 mmol) and phenylboronic acid (0.16 mmol), following the procedure as described for compound A1, to give compound A24 as a white solid in 6% yield. 1H NMR (CDCl3, 400 MHz) δ (ppm) 1.40 (s, 9H), 1.82-1.91 (m, 1H), 2.01-2.13 (m, 1H), 2.35-2.42 (m, 1H), 3.13-3.21 (m, 1H), 3.77-3.84 (m, 1H), 4.70-4.72 (m, 1H), 5.46 (d, J=7.08 Hz, 1H), 6.04 (d, J=7.08 Hz, 1H), 7.31-7.46 (m, 11H), 7.63 (s, 1H), 7.89 (s, 1H), 9.88 (brs, 1H); and MS (ESI, EI+) m/z=546.23 (MH+).

Workup

  1. customto give compound A24 as a white solid in 6% yield

Sources & evidence

ORD record
ord-7149437220e545cc8e54f6a1860bd9e8
Source dataset
uspto-grants-2013_01
Patent number
US08362068B2

Reaction notes

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