HCID 66649651, compound → HCID 66649644, compound

HRID 420311Notes

Reaction equation

HRID 420311 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:38]=[CH:39][CH:40]=1)[CH2:8][N:9]1[C@@H:17]2[C@H:12]([C@H:13]([CH2:20][C:21]3[CH:26]=[C:25]([O:27][CH2:28][C:29]([F:32])([F:31])[F:30])[C:24]([N+:33]([O-])=O)=[C:23]([F:36])[CH:22]=3)[CH2:14][S:15](=[O:19])(=[O:18])[CH2:16]2)[O:11][C:10]1=[O:37])([CH3:4])([CH3:3])[CH3:2]>C1(C)C=CC=CC=1>[NH2:33][C:24]1[C:25]([O:27][CH2:28][C:29]([F:31])([F:32])[F:30])=[CH:26][C:21]([CH2:20][C@H:13]2[C@H:12]3[C@@H:17]([N:9]([CH2:8][C:7]4[CH:38]=[CH:39][CH:40]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=4)[C:10](=[O:37])[O:11]3)[CH2:16][S:15](=[O:19])(=[O:18])[CH2:14]2)=[CH:22][C:23]=1[F:36]

Participants

3

Reactant 1

HCID 66649651HCID 66649651, compound

Product 1

HCID 66649644HCID 66649644, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared in analogous manner as described for example 1j) from (3aR,7S,7aS)-3-(3-tert-butyl-benzyl)-7-[3-fluoro-4-nitro-5-(2,2,2-trifluoro-ethoxy)-benzyl]-5,5-dioxo-hexahydro-1-oxa-5lambda*6*-thia-3-aza-inden-2-one (1.32 g, 2.24 mmol) to yield a white foam: TLC Rf=0.60 (toluene-ETA 85:15); ESIMS [M+NH4]+=576; LCMS RtH1=3.60 min API ESI pos. [M+H]+=559; 1H NMR (600 MHz, DMSO-d6): δ 7.39 (s, 1H), 7.32 (d, 1H), 7.28 (t, 1H), 7.10 (d, 1H), 6.66 (s, 1H), 6.65 (d, 1H), 4.70 (q, 2H), 4.60 (s, 2H), 4.41 (d, 1H), 4.20 (d, 1H), 4.14 (t, 1H), 3.73 (m, 1H), 3.63 (m, 1H), 3.45 (t, 1H), 3.05 (m, 1H), 2.97 (m, 1H), 2.80 (m, 1H), 2.41 (m, 2H), 1.25 (s, 9H).

Workup

  1. customto yield a white foam
  2. customLCMS RtH1=3.60 min API ESI pos

Sources & evidence

ORD record
ord-79fbe83e3c134a588c9ce7903e748567
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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