(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 → (1R,3S,4S,5R)-3-[4-Amino-3-fluoro-5-((R)-2,2,2-trifluoro-1-methoxymethyl-ethoxy)-benzyl]-5-[3-(1-methyl-cyclopropyl)-benzylamino]-1-oxo-tetrahydro-thiopyran-4-ol

HRID 420324Notes

Reaction equation

HRID 420324 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][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]1([C:35]2[CH:36]=[C:37]([CH:40]=[CH:41][CH:42]=2)[CH:38]=O)[CH2:34][CH2:33]1>>[NH2:26][C:14]1[C:15]([O:17][C@H:18]([CH2:23][O:24][CH3:25])[C:19]([F:22])([F:21])[F:20])=[CH:16][C:11]([CH2:10][C@H:7]2[C@H:8]([OH:9])[C@@H:3]([NH:2][CH2:38][C:37]3[CH:40]=[CH:41][CH:42]=[C:35]([C:32]4([CH3:31])[CH2:33][CH2:34]4)[CH:36]=3)[CH2:4][S@:5](=[O:30])[CH2:6]2)=[CH:12][C:13]=1[F:29]

Participants

3

Reactant 2

HCID 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 866280633-(1-Methylcyclopropyl)benzaldehyde

Product 1

HCID 66649698(1R,3S,4S,5R)-3-[4-Amino-3-fluoro-5-((R)-2,2,2-trifluoro-1-methoxymethyl-ethoxy)-benzyl]-5-[3-(1-methyl-cyclopropyl)-benzylamino]-1-oxo-tetrahydro-thiopyran-4-ol

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 3-(1-methyl-cyclopropyl)benzaldehyde to yield the title compound as a yellowish foam: TLC (CH2Cl2-MeOH 9:1) Rf=0.48; HPLC RtG3=1.70 min; ESIMS [M+H]+=559.3; 1H NMR (400 MHz, DMSO-d6): δ 7.22-7.18 (m, 2H), 7.11 (d, 1H), 7.07 (d, 1H), 6.72 (s, 1H), 6.64 (d, 1H), 5.09 (m, 1H), 4.99 (d, 1H), 4.58 (s, 2H), 3.75 (m, 3H), 3.59 (d, 1H), 3.32 (s, 3H), 3.19-3.09 (m, 3H), 2.98 (m, 1H), 2.69 (m, 1H), 2.45-2.25 (m, 4H), 1.36 (s, 3H), 0.83 (m, 2H), 0.72 (m, 2H).

Sources & evidence

ORD record
ord-423f30638b0e4bc4839e107077c25ef1
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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