Water → HCID 178518620, compound

HRID 1007522Notes

Reaction equation

HRID 1007522 reaction equation
[C:1]1([S:7][CH2:8][CH2:9][NH:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([C:17]3[CH:26]=[CH:25][C:20]4[NH:21][C:22](=[O:24])[O:23][C:19]=4[CH:18]=3)[CH2:13][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH2:27]>CO>[C:1]1([S:7]([CH2:8][CH2:9][NH:10][C@H:11]2[CH2:12][CH2:13][C@H:14]([C:17]3[CH:26]=[CH:25][C:20]4[NH:21][C:22](=[O:24])[O:23][C:19]=4[CH:18]=3)[CH2:15][CH2:16]2)=[O:27])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 962Water2×HCID 178518619HCID 178518619, compound

Product 1

HCID 178518620HCID 178518620, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred, ice—Cold, suspension of NaIO4 (0.13 g, 0.62 mmol) in H2O (1.2 mL) was added 6-[trans-4-(2-phenylsulfanylethylamino)cyclohexyl]-3H-benzoxazol-2-one (0.25 g, 0.62 mmol). The viscous reaction mixture was diluted with H2O (1.5 mL), warmed to room temperature, and then further diluted with MeOH (15 mL). After 21 hours, the reaction mixture was concentrated under reduced pressure. Purification by flash chromatography (silica, 89:10:1 CH2Cl2:MeOH:NH4OH) gave the free base of 6-[trans-4-(2-benzenesulfinylethylamino)cyclohexyl]-3H-benzoxazol-2-one, which was converted to the HCl salt (0.13 g, 49%): mp 107-110° C.; IR (KBr): 2936, 2783, 1768, cm−1; 1H NMR (500 MHz, DMSO-d6): δ 9.03 (br s, 2H), 7.74-7.60 (m, 5H), 7.16 (s, 1H), 6.99-6.97 (m, 2H), 3.48-3.43 (m, 1H), 3.33-3.29 (m, 1H), 3.18-3.04 (m, 4H), 2.54-2.52 (m, 2H), 1.86-1.84 (m, 2H), 1.51-1.44 (m, 4H); API-MS (m/z): 385 [M+H]+; HPLC: method A, 7.01 minutes (98.1%); method B, 12.83 minutes (99.2%); Anal. Calcd for C21H24N2O3S.HCl.1.25H2O: C, 56.88; H, 6.25; N, 6.32. Found: C, 56.86; H, 6.18; N, 6.22.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customPurification by flash chromatography (silica, 89:10:1 CH2Cl2:MeOH:NH4OH)

Sources & evidence

ORD record
ord-12682da4e1cc4578bc09637b34012219
Source dataset
uspto-grants-2004_09
Patent number
US06794402B2

Reaction notes

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