(-)-Epichlorohydrin → HCID 25115550, compound

HRID 1640542Notes

Reaction equation

HRID 1640542 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH2:12][NH:13][CH2:14][CH2:15][CH2:16][CH:17]1[O:21][C:20](=[O:22])[N:19]([C:23]3[CH:24]=[CH:25][C:26]4[S:31][CH2:30][C:29](=[O:32])[NH:28][C:27]=4[CH:33]=3)[CH2:18]1)=[N:9][C:8]([O:34][CH3:35])=[CH:7][CH:6]=2.[CH2:36]([C@@H:38]1[O:40][CH2:39]1)[Cl:37]>C1COCC1.CO>[Cl:37][CH2:36][C@H:38]([OH:40])[CH2:39][N:13]([CH2:12][C:11]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:34][CH3:35])[N:9]=2)[N:4]=[CH:3][C:2]=1[F:1])[CH2:14][CH2:15][CH2:16][CH:17]1[O:21][C:20](=[O:22])[N:19]([C:23]2[CH:24]=[CH:25][C:26]3[S:31][CH2:30][C:29](=[O:32])[NH:28][C:27]=3[CH:33]=2)[CH2:18]1

Participants

4

Reactant 2

HCID 2734062(-)-EpichlorohydrinHCID 66736433HCID 66736433, compound

Product 1

HCID 25115550HCID 25115550, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A solution of the compound of Example 78 (0.135 g, 0.27 mmol) in THF/MeOH (1:1, 2 mL) was treated with (R)-epichlorohydrin (0.032 mL, 1.5 eq.). The mixture was heated at 70° C. overnight, concentrated in vacuo and purified by FC (EA/MeOH 19:1+1% NH4OH) to give the title compound as a colourless foam (0.1 g, 52% yield).

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified by FC (EA/MeOH 19:1+1% NH4OH)

Sources & evidence

ORD record
ord-45adec12dfe6467a8c429865dfd6945c
Source dataset
uspto-grants-2012_02
Patent number
US08114867B2

Reaction notes

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