Hydrochloric Acid → (1R,3S,4S,5R)-3-[4-Amino-3-fluoro-5-((R)-2,2,2-trifluoro-1-methoxymethyl-ethoxy)-benzyl]-5-{[5-(2,2-dim ethyl-propyl)-isoxazol-3-ylmethyl]amino}-1-oxo-tetra-hydro-thiopyran-4-ol dihydrochloride

HRID 420326Notes

Reaction equation

HRID 420326 reaction equation
[ClH:1].[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][C@H:18]([CH2:23][O:24][CH3:25])[C:19]([F:22])([F:21])[F:20])[C:14]([N+:26]([O-])=O)=[C:13]([F:29])[CH:12]=2)[CH2:6][S@@:5](=[O:30])[CH2:4]1.[CH3:31][C:32]([CH3:42])([CH3:41])[CH2:33][C:34]1[O:38][N:37]=[C:36]([CH:39]=O)[CH:35]=1.Cl>CCOCC>[ClH:1].[ClH:1].[NH2:26][C:14]1[C:15]([O:17][C@H:18]([CH2:23][O:24][CH3:25])[C:19]([F:22])([F:20])[F:21])=[CH:16][C:11]([CH2:10][C@H:7]2[C@H:8]([OH:9])[C@@H:3]([NH:2][CH2:39][C:36]3[CH:35]=[C:34]([CH2:33][C:32]([CH3:42])([CH3:41])[CH3:31])[O:38][N:37]=3)[CH2:4][S@:5](=[O:30])[CH2:6]2)=[CH:12][C:13]=1[F:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 66649645(1R,3R,4S,5S)-3-amino-5-[3-fluoro-4-nitro-5-((R)-2,2,2-trifluoro-1-methoxymethyl-ethoxy)-benzyl]-1-oxo-tetrahydro-thiopyran-4-ol hydrochlorideHCID 866395455-(2,2-Dimethyl-propyl)-isoxazole-3-carbaldehyde

Product 1

HCID 86639546(1R,3S,4S,5R)-3-[4-Amino-3-fluoro-5-((R)-2,2,2-trifluoro-1-methoxymethyl-ethoxy)-benzyl]-5-{[5-(2,2-dim ethyl-propyl)-isoxazol-3-ylmethyl]amino}-1-oxo-tetra-hydro-thiopyran-4-ol dihydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The title compound can be prepared in an analogous manner as described for example 41 steps c) and d) from (1R,3R,4S,5S)-3-amino-5-[3-fluoro-4-nitro-5-((R)-2,2,2-trifluoro-1-methoxymethyl-ethoxy)-benzyl]-1-oxo-tetrahydro-thiopyran-4-ol hydrochloride and 5-(2,2-dimethyl-propyl)-isoxazole-3-carbaldehyde and subsequent transformation into the hydrochloride salt with 5N HCl in Et2O to afford the title compound as a beige foam: TLC (CH2Cl2-MeOH 9:1) Rf=0.53; HPLC RtG3=1.77 min; ESIMS [M+H]+=566; 1H NMR (400 MHz, DMSO-d6): δ 6.73 (s, 1H), 6.64 (d, 1H), 6.25 (s, 1H), 5.12-5.06 (m, 1H), 4.99 (d, 1H), 4.59 (s, 2H), 3.83-3.68 (m, 4H), 3.33 (s, 3H), 3.17-3.06 (m, 3H), 3.00-2.97 (m, 1H), 2.72-2.68 (m, 1H), 2.63 (s, 2H), 2.45-2.27 (m, 4H), 0.93 (s, 9H).

Sources & evidence

ORD record
ord-fc822e581c5949a5ab65dda4e65cdf95
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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