Triethylamine → HCID 89851813, compound

HRID 627216Notes

Reaction equation

HRID 627216 reaction equation
CC1(C)[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:5]([C:14]([CH2:17][CH3:18])=[CH:15][CH3:16])[CH2:4][O:3]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>CO>[CH2:17]([C:14](=[CH:15][CH3:16])[C@H:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:12])([CH3:11])[CH3:13])[CH2:4][OH:3])[CH3:18]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 89851361(S)-tert-butyl 2,2-dimethyl-4-(pent-2-en-3-yl)oxazolidine-3-carboxylate2×

Product 1

HCID 89851813HCID 89851813, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (S)-tert-butyl 2,2-dimethyl-4-(pent-2-en-3-yl)oxazolidine-3-carboxylate (Intermediate 201, 15.815 g, 58.71 mmol) and p-toluenesulfonic acid monohydrate (3.35 g, 17.61 mmol) in methanol (100 mL) was heated to 85° C. for 3 h. The reaction mixture was cooled to room temperature and triethylamine (8.18 mL, 58.71 mmol) and di-tert-butyl dicarbonate (6.82 mL, 29.35 mmol) were added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure to give a yellow oil. Purification by flash column chromatography (0-100% ethyl acetate/hexanes) afforded the title compound (10.12 g, 75%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto give a yellow oil
  3. customPurification by flash column chromatography (0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-8967a7eada0648b9901ba0d75e439220
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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