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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 216293Generated: October 29, 2026

Ethanol → tert-butyl (2S,3S)-2-[3-({2-[(isopropylamino)methyl]-1,3-thiazol-4-yl}methyl)-2-oxo-1-imidazolidinyl]-3-methylpentanoate

https://huagongshe.com/reaction/216293

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthanolHCID 702—
ReactantIsopropylamineHCID 6363—
ReactantSodium borohydrideHCID 4311764—
ReactantTert-butyl(2s)-2-{3-[(2-formyl-1,3-thiazol-4-yl)methyl]-2-oxo-1-imidazolidinyl}-3-methylbutanoateHCID 87193539—
SolventTolueneHCID 1140—
Producttert-butyl (2S,3S)-2-[3-({2-[(isopropylamino)methyl]-1,3-thiazol-4-yl}methyl)-2-oxo-1-imidazolidinyl]-3-methylpentanoateHCID 66889849—

Reaction Conditions

Temperature70 °C

Reaction Steps

A solution of Example 273D (65 mg) in toluene:ethanol (0.7 mL, 1:1) was treated with isopropylamine (0.14 mL, 10 equivalents), stirred at 70° C. in a capped vial for 2 hrs. The mixture was cooled to 25° C. and NaBH4 (19 mg, 3 equivalents) was added and the mixture was stirred at 25° C. for 3 days. The solvents were evaporated, and the residue was partitioned between ethyl acetate and saturated NaHCO3, the organic layer was separated and washed with brine, dried over MgSO4, filtered and evaporated to give 59 mg of the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08193227B2
Source datasetuspto-grants-2012_06
ORD IDord-a0ed7c62c5e34046ae462240bfbfcf82
Source noteuspto-grants-2012_06