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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1174332Generated: November 1, 2026

2,2-Dimethoxypropane → tert-butyl (4S,5S)-4-benzyl-5-[2-{[(benzyloxy)carbonyl]amino}-3-(4-bromophenyl)propyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

https://huagongshe.com/reaction/1174332

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2,2-DimethoxypropaneHCID 6495—
ReactantTriethylamineHCID 8471—
Reactantbenzyl(3S,4S)-1-(4-bromobenzyl)-4-[(tert-butoxycarbonyl)amino]-3-hydroxy-5-phenylpentylcarbamateHCID 86726232—
Catalystp-Toluenesulfonic acid monohydrateHCID 521998—
Producttert-butyl (4S,5S)-4-benzyl-5-[2-{[(benzyloxy)carbonyl]amino}-3-(4-bromophenyl)propyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylateHCID 6740653254%

Reaction Conditions

Temperature25 °C

Reaction Steps

A solution containing the product from Example 128A (3.37 mmol) in 2,2-dimethoxypropane (35 mL) was treated with p-toluenesulfonic acid monohydrate (0.032 g, 0.17 mmol), stirred at 25° C. for 1 hour, treated with triethylamine (0.14 mL, 1.0 mmol), and the reaction was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated to give the product (1.16 g, 54% yield), which was used without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07834043B2
Source datasetuspto-grants-2010_11
ORD IDord-cc6aac34cc2449429195b8f3eec3a41f
Source noteuspto-grants-2010_11