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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 716533Generated: October 25, 2026

(S,R)-1-(2-tert-butoxycarbonylamino-2-phenylacetyl)-pyrrolidine-2-carboxylic acid → (S,R)-{2-[2-(2-bromo-imidazo[2,1-b]thiazol-6-ylcarbamoyl)-pyrrolidin-1-yl]-2-oxo-1-phenylethyl}-carbamic acid ethyl ester

https://huagongshe.com/reaction/716533

Reaction equation

Participants

RoleNameHCIDCharge
Reactant(S,R)-1-(2-tert-butoxycarbonylamino-2-phenylacetyl)-pyrrolidine-2-carboxylic acidHCID 10089106—
Reactant2-Bromo-imidazo[2,1-b]thiazol-6-ylamine hydrochlorideHCID 67240528—
Reactant(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 esterHCID 86654641—
Product(S,R)-{2-[2-(2-bromo-imidazo[2,1-b]thiazol-6-ylcarbamoyl)-pyrrolidin-1-yl]-2-oxo-1-phenylethyl}-carbamic acid ethyl esterHCID 67240827—

Reaction Steps

Compound 44 was synthesized from compounds 43 (0.377 mmol) and 11 (0.565 mmol), following the procedure as described for compound 12a, at room temperature overnight, to give compound 44 as a yellow oil in 66% yield. 1H NMR (DMSO-d6, 400 MHz) δ (ppm) 1.10 (t, 3H), 1.80 (m, 2H), 1.95 (m, 2H), 3.10 (m, 1H), 3.81 (m, 1H), 3.99 (m, 2H), 4.40 (m, 1H), 5.42 (m, 1H), 7.31 (m, 5H), 7.50 (d, 1H), 7.81 (s, 1H), 8.16 (s, 1H), 10.61 (s, 1H); MS (ESI, EI+) m/z=520-522 (MH+)

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09187496B2
Source datasetuspto-grants-2015_11
ORD IDord-502e7c88027c499587c2ab6cae19819d
Source noteuspto-grants-2015_11