3-Fluorophenol → HCID 57968576, compound

HRID 882769Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13]S(C)(=O)=O)[C@H:9]1[C:18]([N:20]1[CH2:26][CH2:25][CH2:24][N:23]([CH:27]2[CH2:30][CH2:29][CH2:28]2)[CH2:22][CH2:21]1)=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:31][C:32]1[CH:33]=[C:34](O)[CH:35]=[CH:36][CH:37]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([O:13][C:36]2[CH:35]=[CH:34][CH:33]=[C:32]([F:31])[CH:37]=2)[C@H:9]1[C:18]([N:20]1[CH2:26][CH2:25][CH2:24][N:23]([CH:27]2[CH2:30][CH2:29][CH2:28]2)[CH2:22][CH2:21]1)=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

A vial containing a mixture of (2S,3S)-2-(4-cyclobutyl-[1,4]diazepane-1-carbonyl)-3-methanesulfonyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester (106.0 mg, 0.24 mmol), 3-fluorophenol (29.3 mg, 0.26 mmol), and K2CO3 (39.5 mg) in DMF (2.5 mL) was capped and heated for 60 h at 90° C. The mixture was cooled to rt and filtered. The filtrate was concentrated and the residue was purified by FCC to afford the title compound (17 mg, 15%). MS (ESI): mass calcd. for C25H36FN3O4, 461.57; m/z found, 462.3 [M+H]+. 1H NMR (CDCl3): 7.25-7.19 (m, 1H), 6.74-6.64 (m, 2H), 6.64-6.57 (m, 1H), 5.09-4.70 (m, 2H), 3.81-3.49 (m, 6H), 2.90-2.76 (m, 1H), 2.59-2.29 (m, 5H), 2.15-1.72 (m, 7H), 1.64-1.53 (m, 2H), 1.49-1.41 (m, 9H).

Workup

additionA vial containing
customwas capped
temperatureThe mixture was cooled to rt
filtrationfiltered
concentrationThe filtrate was concentrated
customthe residue was purified by FCC

Sources & evidence

ORD record: ord-fdb62e1601bc4cf9acfc51e20aefc882
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236792B2

Reaction notes

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