Dimethylformamide dimethyl acetal → HCID 66719111, compound

HRID 1509068Notes

Reaction equation

HRID 1509068 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18](=[O:26])[CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].CO[CH:30](OC)[N:31]([CH3:33])[CH3:32]>>[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18](=[O:26])[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:30][N:31]([CH3:33])[CH3:32])=[CH:16][CH:17]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 57805516tert-Butyl {1-[4-(phenylacetyl)phenyl]cyclobutyl}carbamate

Product 1

HCID 66719111HCID 66719111, compound

Procedure

A solution of tert-butyl(1-(4-(2-phenylacetyl)phenyl)cyclobutyl)carbamate (25.0 g, 68 mmol) in N,N-dimethylformamide dimethylacetal (150 mL) was heated to 80° C. under a nitrogen atmosphere for 18 hours. The resulting brown solution was allowed to cool to room temperature and concentrated to dryness under reduced pressure to give the desired product as a yellow/brown solid (30.6 g, quantitative yield). 1H-NMR (500 MHz, CDCl3) δ 7.14-7.48 (10H, m), 5.09 (1H, br s), 2.74 (6H, s), 2.45-2.60 (4H, m), 2.04-2.16 (1H, m), 1.80-1.90 (1H, m), 1.10-1.52 (9H, br m).

Workup

  1. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-a6ca18f068114398a8d8ef3fad4bf01c
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

Loading…