Acetic Acid → HCID 71204759, compound

HRID 2273110Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of methyl 4-((S)-1-((R)-piperidine-2-carboxamido)ethyl)benzoate (D12) (50 mg, 0.17 mmol) and 3-(trifluoromethoxy)benzaldehyde (0.025 ml, 0.20 mmol), NaBH(OAc)3 (109 mg, 0.52 mmol) and catalytic CH3COOH in DCM (12 ml) was heated at 100° C. (2 cycles of 5 min each) under microwave irradiation. The resulting mixture was purified by SPE-Si (2 g) eluting with a mixture DCM/AcOEt from 100/0 to 80/20. Collected fractions after solvent evaporation afforded the title compound (D25) (52 mg).

Workup

customunder microwave irradiation
customThe resulting mixture was purified by SPE-Si (2 g)
washeluting with a mixture DCM/AcOEt from 100/0 to 80/20
customCollected fractions after solvent evaporation

Sources & evidence

ORD record: ord-8740a871a3f646b490fa738019975bd1
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120824B2

Reaction notes

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