3-tert-butylbenzaldehyde → HCID 131729382, compound

HRID 420309Notes

Reaction equation

Cl.[NH2:2][C@@H:3]1[C@@H:8]([OH:9])[C@H:7]([CH2:10][C:11]2[CH:16]=[C:15]([O:17][CH2:18][C:19]([F:22])([F:21])[F:20])[C:14]([N+:23]([O-:25])=[O:24])=[C:13]([F:26])[CH:12]=2)[CH2:6][S:5](=[O:28])(=[O:27])[CH2:4]1.[C:29]([C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=1)[CH:36]=O)([CH3:32])([CH3:31])[CH3:30]>>[C:29]([C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=1)[CH2:36][NH:2][C@@H:3]1[C@@H:8]([OH:9])[C@H:7]([CH2:10][C:11]2[CH:16]=[C:15]([O:17][CH2:18][C:19]([F:22])([F:20])[F:21])[C:14]([N+:23]([O-:25])=[O:24])=[C:13]([F:26])[CH:12]=2)[CH2:6][S:5](=[O:27])(=[O:28])[CH2:4]1)([CH3:32])([CH3:30])[CH3:31]

Participants

Reactant 2

HCID 101925883-tert-butylbenzaldehyde

HCID 131729384HCID 131729384, compound

Product 1

HCID 131729382HCID 131729382, compound

Procedure

The title compound was prepared in analogous manner as described for example 1h) from (3R,4S,5S)-3-Amino-5-[4-nitro-3-fluoro-5-(2,2,2-trifluoro-ethoxy)-benzyl]-1,1-dioxo-hexahydro-1lambda*6*-thiopyran-4-ol hydrochloride salt (1.26 g, 2.78 mmol) and 3-tert-butyl benz-aldehyde (0.361 g, 2.26 mmol); ESIMS [M+H]+=563, UPLC RtD=1.576 min, 1H NMR (600 MHz, DMSO-d6): δ 7.35 (s, 1H), 7.27-7.21 (m, 2H), 7.15 (m, 2H), 7.10 (d, 1H), 5.32 (d, 1H), 5.01 (q, 2H), 3.81 (m, 1H), 3.63 (m, 1H), 3.38 (m, 1H), 3.20 (m, 1H), 3.10 (m, 1H), 3.05-2.98 (m, 2H), 2.80 (m, 2H), 2.63 (m, 1H), 2.41 (s, 1H), 2.14 (m, 1H), 1.25 (s, 9H).

Workup

customESIMS [M+H]+=563, UPLC RtD=1.576 min, 1H NMR (600 MHz, DMSO-d6): δ 7.35 (s, 1H), 7.27-7.21 (m, 2H), 7.15 (m, 2H), 7.10 (d, 1H), 5.32 (d, 1H), 5.01 (q, 2H), 3.81 (m, 1H), 3.63 (m, 1H), 3.38 (m, 1H), 3.20 (m, 1H), 3.10 (m, 1H), 3.05-2.98 (m, 2H), 2.80 (m, 2H), 2.63 (m, 1H), 2.41 (s, 1H), 2.14 (m, 1H), 1.25 (s, 9H)

Sources & evidence

ORD record: ord-623a6514744c44e8aa45332a39a87017
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093406B2

Reaction notes

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