tert-Butanol → HCID 66801718, compound

HRID 2366307Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([F:15])[C:10]=1[C:11]([O:13][CH3:14])=[O:12])C(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:23])C=CC=CC=1.C([N:35]([CH2:38]C)CC)C.[C:40]([OH:44])([CH3:43])([CH3:42])[CH3:41]>>[C:40]([O:44][C:38]([NH:35][C:4]1[CH:8]=[C:9]([F:15])[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:2]([Cl:1])[CH:3]=1)=[O:23])([CH3:43])([CH3:42])[CH3:41]

Participants

Reactant 4

HCID 6386tert-Butanol

HCID 8471Triethylamine

HCID 199401P,P-Diphenylphosphinic azide

HCID 66801910HCID 66801910, compound

Product 1

HCID 66801718HCID 66801718, compoundYield 90.2%

Conditions

Temperature: 85 °C

Procedure

To a solution of 3-chloro-5-fluoro-4-methoxycarbonyl-benzoic acid (5.55 g, 23.84 mmol) in tert-butanol (48 mL) was added diphenyl phosphorylazide (7.22 g, 26.2 mmol) and triethylamine (2.65 g, 26.2 mmol). The mixture was heated at 85° C. for 20 hours, then concentrated via rotavap. The crude product was purified by silica gel chromatography (0-20% EtOAc/hexane) to give the title compound. (6.53 g, 90.2% yield) as a colorless oil. 1H NMR (400 MHz, CD2Cl2) δ 7.32 (dd, J=11.7, 1.7 Hz, 1H), 7.28 (s, 1H), 7.05 (s, 1H), 3.95 (s, 3H), 1.54 (s, 9H). LCMS (ESI) m/z 304.0 [M+H+].

Workup

concentrationconcentrated via rotavap
customThe crude product was purified by silica gel chromatography (0-20% EtOAc/hexane)

Sources & evidence

ORD record: ord-268299444f324cdf87d3b5201cd98233
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697708B2

Reaction notes

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