3-tert-butylbenzaldehyde → HCID 66649701, compound

HRID 420321Notes

Reaction equation

HRID 420321 reaction equation
[OH:1][C:2](C(F)(F)F)=O.[NH2:8][C@@H:9]1[C@@H:14]([OH:15])[C@H:13]([CH2:16][C:17]2[CH:22]=[C:21]([O:23][C@@:24]([CH3:31])(OC)[C:25]([F:28])([F:27])[F:26])[C:20]([N+:32]([O-:34])=[O:33])=[C:19]([F:35])[CH:18]=2)[CH2:12][S@:11](=[O:36])[CH2:10]1.[C:37]([C:41]1[CH:42]=[C:43]([CH:46]=[CH:47][CH:48]=1)[CH:44]=O)([CH3:40])([CH3:39])[CH3:38]>>[C:37]([C:41]1[CH:42]=[C:43]([CH:46]=[CH:47][CH:48]=1)[CH2:44][NH:8][C@@H:9]1[C@@H:14]([OH:15])[C@H:13]([CH2:16][C:17]2[CH:22]=[C:21]([O:23][C@H:24]([CH2:31][O:1][CH3:2])[C:25]([F:26])([F:28])[F:27])[C:20]([N+:32]([O-:34])=[O:33])=[C:19]([F:35])[CH:18]=2)[CH2:12][S@:11](=[O:36])[CH2:10]1)([CH3:40])([CH3:39])[CH3:38]

Participants

3

Reactant 2

HCID 101925883-tert-butylbenzaldehydeHCID 86639544HCID 86639544, compound

Product 1

HCID 66649701HCID 66649701, compound

Procedure

The title compound was prepared in an analogous manner as described for example 1h, starting from (1S,3R,4S,5S)-3-amino-5-[3-fluoro-4-nitro-5-((R)-2,2,2-trifluoro-1-methoxy-methyl-ethoxy)-benzyl]-1-oxo-tetrahydro-thiopyran-4-ol TFA salt (310 mg, 0.7 mmol) and 3-tert-butyl-benzaldehyde and was obtained after purification by flash-chromatography (hexane-(EtOAc-MeOH 9:1) gradient) as a light yellow foam: TLC (EtOAc-MeOH 9:1) Rf=0.38; HPLC RtH1=1.05 min; ESIMS [M+H]+=591; 1H NMR (600 MHz, CDCl3): δ 7.36 (s, 1H), 7.28 (s, 1H), 7.23 (m, 2H), 7.13 (d, 1H), 7.11 (d, 1H), 5.66 (m, 1H), 5.16 (d, 1H), 3.83-3.79 (m, 2H), 3.69 (dd, 1H), 3.63 (d, 1H), 3.55 (m, 1H), 3.30 (s, 3H), 3.14 (m, 2H), 3.00 (d, 1H), 2.55 (m, 1H), 2.5-2.4 (m, 3H), 1.95 (m, 1H), 1.25 (s, 9H).

Workup

  1. customwas obtained
  2. customafter purification by flash-chromatography (hexane-(EtOAc-MeOH 9:1) gradient) as a light yellow foam
  3. customHPLC RtH1=1.05 min

Sources & evidence

ORD record
ord-126fd33d37c24166a086f0b9144974b6
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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