HCID 66649639, compound → HCID 66649777, compound

HRID 420334Notes

Reaction equation

HRID 420334 reaction equation
[NH2:1][C@@H:2]1[C@@H:7]([OH:8])[C@H:6]([CH2:9][C:10]2[CH:15]=[C:14]([O:16][C@@:17]([CH3:24])([O:22][CH3:23])[C:18]([F:21])([F:20])[F:19])[C:13]([NH2:25])=[C:12]([F:26])[CH:11]=2)[CH2:5][S@@:4](=[O:27])[CH2:3]1.[C:28]([C:32]1[CH:33]=[C:34]([CH:37]=[C:38]([O:40][CH3:41])[CH:39]=1)[CH:35]=O)([CH3:31])([CH3:30])[CH3:29]>>[NH2:25][C:13]1[C:14]([O:16][C@@:17]([CH3:24])([O:22][CH3:23])[C:18]([F:21])([F:19])[F:20])=[CH:15][C:10]([CH2:9][C@H:6]2[C@H:7]([OH:8])[C@@H:2]([NH:1][CH2:35][C:34]3[CH:37]=[C:38]([O:40][CH3:41])[CH:39]=[C:32]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:33]=3)[CH2:3][S@:4](=[O:27])[CH2:5]2)=[CH:11][C:12]=1[F:26]

Participants

3

Reactant 2

HCID 66649639HCID 66649639, compoundHCID 86639552HCID 86639552, compound

Product 1

HCID 66649777HCID 66649777, compound

Procedure

The title compound was prepared in an analogous manner as described for example 48g starting from (1R,3R,4S,5S)-3-amino-5-[4-amino-3-fluoro-5-((R)-2,2,2-trifluoro-1-methoxy-methyl-ethoxy)-benzyl]-1-oxo-tetrahydro-thiopyran-4-ol (example 48f) and 3-tert-butyl-5-methoxy-benzaldehyde and was obtained after purification by column chromatography on silica gel with (EtOAc/5% MeOH) 70-0% hexane as a colorless foam: TLC (AcOEt-MeOH 19:1) Rf=0.43; HPLC RtH1=2.55 min; ESIMS [M+H]+=591; 1H NMR (600 MHz, DMSO-d6): δ 6.92 (s, 1H), 6.75 (s, 2H), 6.72 (s, 1H), 6.67 (d, 3H), 5.01 (br s, 1H), 4.60 (br s, 2H), 3.77-3.68 (m, 3H), 3.73 (s, 3H), 3.61 (d, 1H), 3.30 (s 3H), 3.15 (m, 1H), 3.10 (m, 2H), 2.96 (m, 1H), 2.70 (m, 1H), 2.50-2.25 (m, 5H), 1.24 (s, 9H).

Workup

  1. customwas obtained
  2. customafter purification by column chromatography on silica gel with (EtOAc/5% MeOH) 70-0% hexane as a colorless foam
  3. customHPLC RtH1=2.55 min

Sources & evidence

ORD record
ord-12315f51a5434b789600cc93134e7418
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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