Sodium hydride → 1-t-Butoxycarbonylmethyl-3-azido-8-methylperhydroazocin-2-one

HRID 279794

Reaction equation

[N:1]([CH:4]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]([CH3:12])[NH:6][C:5]1=[O:13])=[N+:2]=[N-:3].I[CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].[H-].[Na+]>>[C:19]([O:18][C:16]([CH2:15][N:6]1[CH:7]([CH3:12])[CH2:8][CH2:9][CH2:10][CH2:11][CH:4]([N:1]=[N+:2]=[N-:3])[C:5]1=[O:13])=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

Reactant 3

HCID 24758Sodium hydride

HCID 11021060Tert-butyl 2-iodoacetate

HCID 136083123-Azido-8-methylperhydroazocin-2-one

Product 1

HCID 233225351-t-Butoxycarbonylmethyl-3-azido-8-methylperhydroazocin-2-one

Procedure

React 5.65 g of this azide with 7.9 g t-butyl iodoacetate and 0.82 g sodium hydride as described in Example 1 to obtain 1-t-butoxycarbonylmethyl-3-azido-8-methylperhydroazocin-2-one, which can be purified by chromatography over silica gel. NMR (CCl4, TMS): δ 1.0-2.2 (m); δ 1.3 (d); δ 1.45 (s); δ 3.45 (d, J=16h3); δ 3.95 (d, J-16h3); δ 4.3-5.1 (m).

Sources & evidence

ORD record: ord-b484811a8fa94bda97e3b37dc6d321c0
Source dataset: uspto-grants-1986_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04587050

Linked notes

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