HCID 66649701, compound → HCID 66649683, compound

HRID 420322Notes

Reaction equation

HRID 420322 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:38]=[CH:39][CH:40]=1)[CH2:8][NH:9][C@@H:10]1[C@@H:15]([OH:16])[C@H:14]([CH2:17][C:18]2[CH:23]=[C:22]([O:24][C@H:25]([CH2:30][O:31][CH3:32])[C:26]([F:29])([F:28])[F:27])[C:21]([N+:33]([O-])=O)=[C:20]([F:36])[CH:19]=2)[CH2:13][S@:12](=[O:37])[CH2:11]1)([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.CO>[NH2:33][C:21]1[C:22]([O:24][C@H:25]([CH2:30][O:31][CH3:32])[C:26]([F:29])([F:27])[F:28])=[CH:23][C:18]([CH2:17][C@H:14]2[C@H:15]([OH:16])[C@@H:10]([NH:9][CH2:8][C:7]3[CH:38]=[CH:39][CH:40]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=3)[CH2:11][S@@:12](=[O:37])[CH2:13]2)=[CH:19][C:20]=1[F:36]

Participants

3

Reactant 1

HCID 66649701HCID 66649701, compound

Product 1

HCID 66649683HCID 66649683, compound

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

The title compound was prepared in an analogous manner as described for example 41d) from (1S,3R,4S,5S)-3-(3-tert-butyl-benzylamino)-5-[3-fluoro-4-nitro-5-((R)-2,2,2-trifluoro-1-methoxymethyl-ethoxy)-benzyl]-1-oxo-tetrahydro-thiopyran-4-ol as an amorphous solid: TLC (EtOAc-MeOH 9:1) Rf=0.48; HPLC RtH1=0.91 min; ESIMS [M+H]+=561; 1H NMR (600 MHz, CDCl3): δ 7.36 (s, 1H), 7.24 (m, 2H), 7.13 (d, 1H), 6.74 (s, 1H), 6.65 (d, 1H), 5.15 (s, 1H), 5.06 (s, 1H), 4.58 (s, 2H), 3.83-3.79 (m, 2H), 3.73 (m, 2H), 3.63 (dd, 1H), 3.53 (d, 1H), 3.30 (s, 3H), 3.03 (m, 1H), 2.97 (m, 2H), 2.49-2.32 (m, 4H), 1.70-2.62 (m, 1H), 1.25 (s, 9H).

Workup

  1. customHPLC RtH1=0.91 min

Sources & evidence

ORD record
ord-82585f12d46a4d588b3d82d073c34960
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

Loading…