HCID 68157628, compound → HCID 68157006, compound

HRID 243001Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([NH:12][C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[NH:20][C:21](=O)[C@@H:22]([NH:24][C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])[CH3:23])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CC(O)=O>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([N:12]2[C:13]3[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=3[N:20]=[C:21]2[C@@H:22]([NH:24][C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])[CH3:23])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 3-[2-((S)-2-benzyloxycarbonylaminopropionylamino)-5-fluoro-phenylamino]azetidine-1-carboxylic acid tert-butyl ester (15.52 mmol) in AcOH (110 mL) was heated at 60° C. for 18 h, at 70° C. for 24 h and then at 80° C. for 6 h. The volatiles were removed in vacuo and the resulting residue partitioned between EtOAc and a saturated aqueous solution of NaHCO3. The aqueous phase was further extracted with EtOAc (×3) and the combined organic fractions washed with water, followed by brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-60% EtOAc in cyclohexane) to afford the title compound as a yellow oil (3.23 g, 44%). LCMS (Method J): RT 3.60 min [M+H]+ 469.1.

Workup

customThe volatiles were removed in vacuo
customthe resulting residue partitioned between EtOAc
extractionThe aqueous phase was further extracted with EtOAc (×3)
washthe combined organic fractions washed with water
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-60% EtOAc in cyclohexane)

Sources & evidence

ORD record: ord-344a51c0435e47708c70fe3ef26a5fdf
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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