Dimethylformamide dimethyl acetal → HCID 131729361, compound

HRID 420271Notes

Reaction equation

[NH2:1][C:2]1[C:31]([I:32])=[CH:30][C:5]([CH2:6][C@H:7]2[C@H:15]3[C@@H:11]([N:12]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:19]=4)[C:13](=[O:16])[O:14]3)[CH2:10][S:9](=[O:29])(=[O:28])[CH2:8]2)=[CH:4][C:3]=1[F:33].CO[CH:36](OC)[N:37]([CH3:39])[CH3:38]>C1(C)C=CC=CC=1>[C:24]([C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[CH2:17][N:12]1[C@@H:11]2[C@H:15]([C@H:7]([CH2:6][C:5]3[CH:30]=[C:31]([I:32])[C:2]([N:1]=[CH:36][N:37]([CH3:39])[CH3:38])=[C:3]([F:33])[CH:4]=3)[CH2:8][S:9](=[O:28])(=[O:29])[CH2:10]2)[O:14][C:13]1=[O:16])([CH3:27])([CH3:25])[CH3:26]

Participants

Conditions

Temperature: 150 °C

Procedure

To a suspension of (3aR,7S,7aS)-7-(4-amino-3-fluoro-5-iodo-benzyl)-3-(3-tert-butyl-benzyl)-5,5-dioxo-hexahydro-1-oxa-5lambda*6*-thia-3-aza-inden-2-one (2.0 g, 3.2 mmol) in toluene (20 mL) was added N,N-dimethylformamid-dimethylacetal (1.18 g, 9.6 mmol) and the reaction mixture was heated in the microwave oven for 0.5 h at 150° C. After evaporation the residue was purified by chromatography (CombiFlash, 40 g silica gel, hexane-EtOAc 10:1 to EtOAc) to yield the title compound as beige crystals: TLC (hexane-EtOAc 1:1) Rf=0.39; HPLC RtA=1.92 min; ESIMS [M+H]+=641; 1H NMR (400 MHz, CDCl3): δ 7.58 (d, 1H), 7.35 (m, 3H), 7.09 (d, 1H), 6.82 (dd, 1H), 4.54 (d, 1H), 4.33 (d, 1H), 3.83 (dt, 1H), 3.76 (t, 1H), 3.1 (m, 2H), 3.08 (s, 3H), 3.02 (s, 3H), 2.83 (t, 1H), 2.74 (dd, 1H), 2.58 (m, 2H), 1.31 (s, 9H).

Workup

customAfter evaporation the residue
customwas purified by chromatography (CombiFlash, 40 g silica gel, hexane-EtOAc 10:1 to EtOAc)

Sources & evidence

ORD record: ord-33c539dbbe8e4f33b694eca84622e845
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093406B2

Reaction notes

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