Methoxyacetyl chloride → HCID 131729374, compound

HRID 420296Notes

Reaction equation

HRID 420296 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:36]=[CH:37][CH:38]=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]([F:27])[C:24]([NH:28][C:29](=[O:32])[CH2:30][Cl:31])=[C:23]([CH2:33][CH3:34])[CH:22]=3)[CH2:14][S:15](=[O:19])(=[O:18])[CH2:16]2)[O:11]C1=O)([CH3:4])([CH3:3])[CH3:2].[CH3:39][O:40]CC(Cl)=O>>[ClH:31].[C:1]([C:5]1[CH:6]=[C:7]([CH:36]=[CH:37][CH:38]=1)[CH2:8][NH:9][C@H:17]1[CH2:16][S:15](=[O:19])(=[O:18])[CH2:14][C@@H:13]([CH2:20][C:21]2[CH:26]=[C:25]([F:27])[C:24]([NH:28][C:29](=[O:32])[CH2:30][O:40][CH3:39])=[C:23]([CH2:33][CH3:34])[CH:22]=2)[C@@H:12]1[OH:11])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 96623Methoxyacetyl chlorideHCID 131729372HCID 131729372, compound

Product 1

HCID 131729374HCID 131729374, compound

Procedure

The title compound was prepared in analogous manner as described for example 8q and 8r from N-{4-[(3aR,7S,7aS)-3-(3-tert-butyl-benzyl)-2,5,5-trioxo-octahydro-1-oxa-5lambda*6*-thia-3-aza-inden-7-ylmethyl]-2-ethyl-6-fluoro-phenyl}-2-chloro-acetamide and methoxy-acetyl chloride to yield after preparative HPLC purification (Sunfire C18 OBD 5 μm, 100×30, 5-100% ACN in water+0.1% TFA gradient, 25 min) the title compound as a light yellow amorphous solid: TLC (EtOAc-MeOH 9:1) Rf=0.56; UPLC RtD=1.298 min; ESIMS [M+H]+=535; 1H NMR (600 MHz, DMSO-d6): δ 9.99 (s, 1H), 9.31 (s, 1H), 9.08 (s, 1H), 7.68 (s, 1H), 7.44 (dd, 1H), 7.39 (m, 3H), 6.96 (d, 1H), 6.92 (s, 1H), 6.23 (s, 1H), 4.23 (m, 4H), 4.01 (s, 2H), 3.91 (d, 1H), 3.66 (m, 2H), 3.38 (s, 3H), 3.26 (dd, 1H), 3.17 (m, 2H), 2.76 (dd, 1H), 2.52 (m, 3H), 2.10 (m, 1H), 1.29 (s, 9H), 1.08 (t, 3H).

Workup

  1. customto yield
  2. customafter preparative HPLC purification (Sunfire C18 OBD 5 μm, 100×30, 5-100% ACN in water+0.1% TFA gradient, 25 min) the title compound as a light yellow amorphous solid
  3. customUPLC RtD=1.298 min

Sources & evidence

ORD record
ord-daf0706536cc499ba8b821cb6015cc02
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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