Chloroform → HCID 11552200, compound

HRID 19477Notes

Reaction equation

HRID 19477 reaction equation
C([NH:4][C:5]1[N:6]=[C:7]([O:33][CH:34]([CH3:36])[CH3:35])[C:8]2[S:13][C:12](=[O:14])[N:11]([C@@H:15]3[O:27][C@H:26]([CH2:28][O:29]C(=O)C)[C@@H:21]([O:22]C(=O)C)[C@H:16]3[O:17]C(=O)C)[C:9]=2[N:10]=1)(=O)C.C([O-])([O-])=O.[K+].[K+].C1COCC1.C(Cl)(Cl)Cl>CO>[NH2:4][C:5]1[N:6]=[C:7]([O:33][CH:34]([CH3:36])[CH3:35])[C:8]2[S:13][C:12](=[O:14])[N:11]([C@@H:15]3[O:27][C@H:26]([CH2:28][OH:29])[C@@H:21]([OH:22])[C@H:16]3[OH:17])[C:9]=2[N:10]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 68563172HCID 68563172, compound

Product 1

HCID 11552200HCID 11552200, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 27 (600 mg, 1.14 mmol) was dissolved in methanol (15 ml) under a dry nitrogen atmosphere. K2CO3 (31.5 mg, 0.2 mmol) was added and the mixture was stirred for 18 h periodically being monitored by TLC (1:1 THF:Chloroform). The reaction mixture was concentrated under vacuum and purified by flash column chromatography (3% methanol in chloroform). The isolated solid was triturated with ethyl ether yielding 210 mg (51%) of pure 28 as a white solid: 1H NMR (400 MHz, d6-DMSO) δ 6.83 (s, 2H), 5.86 (d, J=5.2 Hz, 1H), 5.34 (m, 1H), 5.26 (d, J=5.6 Hz, 2H), 4.95 (d, J=5.6 Hz, 1H), 4.77 (m, 1H), 4.67 (m, 1H), 4.09 (m, 1H), 3.75 (m, 1H), 3.58 (m, 1H), 3.43 (m, 1H), 1.29 (d, J=6.4 Hz, 6H); MS (+)-ES [M+H]+ m/z 359, [2M+H]+ m/z 717.3. Rf=0.2 (50% THF—CHCl3). Elemental analysis for C13H18N4O16S: calc'd: C, 43.57; H, 5.06; N, 15.63; S, 8.95. Found: C, 43.39; H, 5.07; N, 15.45; S, 8.82.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. custompurified by flash column chromatography (3% methanol in chloroform)
  3. customThe isolated solid was triturated with ethyl ether yielding 210 mg (51%) of pure 28 as a white solid

Sources & evidence

ORD record
ord-ec7423718aa940c9b4cb76f11e29b529
Source dataset
uspto-grants-2010_06
Patent number
US07745415B2

Reaction notes

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