{(1R,3R,4S,5S)-5-[3-fluoro-4-nitro-5-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-benzyl]-4-hydroxy-1-oxo-tetrahydro-thiopyran-3-yl}-carbamic acid tert-butyl ester → (1R,3R,4S,5S)-3-Amino-5-[3-fluoro-4-nitro-5-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-benzyl]-1-oxo-tetrahydro-thiopyran-4-ol

HRID 420337Notes

Reaction equation

HRID 420337 reaction equation
C(OC(=O)[NH:7][C@@H:8]1[C@@H:13]([OH:14])[C@H:12]([CH2:15][C:16]2[CH:21]=[C:20]([O:22][C@@H:23]([CH3:28])[C:24]([F:27])([F:26])[F:25])[C:19]([N+:29]([O-:31])=[O:30])=[C:18]([F:32])[CH:17]=2)[CH2:11][S@@:10](=[O:33])[CH2:9]1)(C)(C)C>C(Cl)Cl.CO.C(O)(C)=O.O>[NH2:7][C@@H:8]1[C@@H:13]([OH:14])[C@H:12]([CH2:15][C:16]2[CH:21]=[C:20]([O:22][C@@H:23]([CH3:28])[C:24]([F:27])([F:25])[F:26])[C:19]([N+:29]([O-:31])=[O:30])=[C:18]([F:32])[CH:17]=2)[CH2:11][S@@:10](=[O:33])[CH2:9]1

Participants

3

Reactant 1

HCID 66649573{(1R,3R,4S,5S)-5-[3-fluoro-4-nitro-5-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-benzyl]-4-hydroxy-1-oxo-tetrahydro-thiopyran-3-yl}-carbamic acid tert-butyl ester

Product 1

HCID 66649569(1R,3R,4S,5S)-3-Amino-5-[3-fluoro-4-nitro-5-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-benzyl]-1-oxo-tetrahydro-thiopyran-4-ol

Reagents, catalysts & solvents 1

HCID 18914200Dichloromethane methanol acetic acid waterSolvent

Procedure

The title compound was prepared in an analogous manner as described for example 1g, starting from {(1R,3R,4S,5S)-5-[3-fluoro-4-nitro-5-((S)-2,2,2-trifluoro-1-methyl-ethoxy)-benzyl]-4-hydroxy-1-oxo-tetrahydro-thiopyran-3-yl}-carbamic acid tert-butyl ester and was obtained as a light yellow foam: TLC (CH2Cl2-MeOH-AcOH-H2O 180:20:2:1) Rf=0.10; HPLC RtA=1.50 min; ESIMS [M+H]+=415; 1H NMR (600 MHz, DMSO-d6): δ 8.09 (s, 3H), 7.29 (s, 1H), 7.14 (d, 1H), 6.02 (s broad, 1H), 5.48 (m, 1H), 3.56 (m, 1H), 3.30 (t, 1H), 3.16 (m, 2H), 2.89 (d, 1H), 2.76 (t, 1H), 2.72 (dd, 1H), 2.5-2.6 (m, 2H), 1.46 (d, 3H).

Workup

  1. customwas obtained as a light yellow foam
  2. customHPLC RtA=1.50 min

Sources & evidence

ORD record
ord-0515fbf36fa043939d3efbb22e5e9c9d
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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