(-)-Glycidol → HCID 66737338, compound

HRID 1640541Notes

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]1[O:38][C@H:37]1[CH2:39][OH:40]>C1COCC1.CO>[OH:38][C@@H:37]([CH2:39][OH:40])[CH2:36][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

Conditions

Temperature: 70 °C

Procedure

A solution of the compound of Example 78 (0.05 g, 0.1 mmol) in THF/MeOH (1:1, 0.5 mL) was treated with (S)-glycidol (0.06 mL, 5 eq.). The mixture was heated at 70° C. for 3 h, concentrated in vacuo and purified by FC (EA/MeOH 19:1+1% NH4OH) to give the title compound as a colourless solid (0.03 g, 52% yield).

Workup

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

Sources & evidence

ORD record: ord-8de37bfc421a45ca9cd5254053f42609
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08114867B2

Reaction notes

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