1,2-Dichloroethane → HCID 53657970, compound

HRID 2084537Notes

Reaction equation

[F:1][C:2]1[C:7]([OH:8])=[C:6]([F:9])[C:5]([F:10])=[C:4]([F:11])[C:3]=1[F:12].[C:13]([O:17][C:18]([NH:20][C@@H:21]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:22](O)=[O:23])=[O:19])([CH3:16])([CH3:15])[CH3:14].CN1CCOCC1.C(Cl)CCl>CCOC(C)=O>[F:1][C:2]1[C:7]([O:8][C:22](=[O:23])[C@@H:21]([NH:20][C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19])[C:25]([CH3:28])([CH3:27])[CH3:26])=[C:6]([F:9])[C:5]([F:10])=[C:4]([F:11])[C:3]=1[F:12]

Participants

Conditions

Temperature: 0 °C

Procedure

Pentafluorophenol (8.75 g, 47.5 mmol) dissolved in EtOAc (5 mL) was added to a solution of 2(S)-tert-butoxycarbonylamino-3,3-dimethyl-butyric acid (10 g, 43 mmol) in EtOAC (35 mL) and the mixture cooled to 0° C. NMM (4.75 mL, 43 mmol) followed by EDC (9.12 g, 47.6 mmol) were added to this cooled solution and the reaction mixture was then allowed to warm to room temperature and stirred overnight. The reaction mixture was then diluted with EtOAc (200 mL) and washed with 1M HCl (2×200 mL), 1M Na2CO3 (3×200 mL) and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (SiO2, 10% EtOAc in hexanes) to give the title compound as a white solid (12.03 g, 70%).

Workup

additionwere added to this cooled solution
temperatureto warm to room temperature
washwashed with 1M HCl (2×200 mL), 1M Na2CO3 (3×200 mL) and brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography (SiO2, 10% EtOAc in hexanes)

Sources & evidence

ORD record: ord-91f61d0b04a54453a1bc2b3a1b6fff1d
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06716878B1

Reaction notes

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