Chlorosuccinimide → HCID 131729375, compound

HRID 420297Notes

Reaction equation

HRID 420297 reaction equation
[NH2:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][C@H:7]2[C@H:15]3[C@@H:11]([N:12]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:19]=4)[C:13](=[O:16])[O:14]3)[CH2:10][S:9](=[O:29])(=[O:28])[CH2:8]2)=[CH:4][C:3]=1[F:32].[Cl:33]N1C(=O)CCC1=O>C(#N)C>[NH2:1][C:2]1[C:3]([F:32])=[CH:4][C:5]([CH2:6][C@H:7]2[C@H:15]3[C@@H:11]([N:12]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([CH3:26])([CH3:27])[CH3:25])[CH:19]=4)[C:13](=[O:16])[O:14]3)[CH2:10][S:9](=[O:28])(=[O:29])[CH2:8]2)=[CH:30][C:31]=1[Cl:33]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 66649435HCID 66649435, compound

Product 1

HCID 131729375HCID 131729375, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (3aR,7S,7aS)-7-(4-amino-3-fluoro-benzyl)-3-(3-tert-butyl-benzyl)-5,5-dioxo-hexahydro-1-oxa-5lambda*6*-thia-3-aza-inden-2-one (4.0 g, 8.69 mmol, example 81) and N-chlorosuccinimide (1.276 g, 9.55 mmol) in ACN (130 mL) was heated at reflux for 2 h. The reaction mixture was evaporated and the residue was purified by chromatography (Combi Flash, 120 g silicagel, hexane-EtOAc) to provide the title compound as a colorless solid: TLC (toluene-EtOAc 3:1) Rf=0.42; UPLC RtD=1.887 min; [M+NH4]+=512, 514; 1H NMR (600 MHz, DMSO-d6): δ 7.38 (s, 1H), 7.32 (d, 1H), 7.27 (t, 1H), 7.13 (d, 1H), 6.93 (s, 1H), 6.89 (d, 1H), 5.28 (s, 2H), 4.42 (d, 1H), 4.21 (d, 1H), 4.11 (t, 1H), 3.68 (m, 2H), 3.46 (t, 1H), 3.05 (m, 2H), 2.78 (d, 1H), 2.50 (m, 2H), 1.26 (s, 9H).

Workup

  1. temperatureat reflux for 2 h
  2. customThe reaction mixture was evaporated
  3. customthe residue was purified by chromatography (Combi Flash, 120 g silicagel, hexane-EtOAc)

Sources & evidence

ORD record
ord-f61f6726669045d1b0be52c143f7bc08
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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