(4R,4aR)-((E)-3,3-dimethyl-but-1-enyl)-7-methoxy-2,2-dimethyl-tetrahydro-furo[3,2-d][1,3]dioxin-6-one → (R)-N-[(3S,6R)-6-(6-azido-hexyloxy)-1-methyl-2-oxo-azepan-3-yl]-2-[(4R,5R,6R)-6-((E)-3,3-dimethyl-but-1-enyl)-5-hydroxy-2,2-dimethyl-[1,3]dioxan-4-yl]-2-methoxy-acetamide

HRID 2224028Notes

Reaction equation

HRID 2224028 reaction equation
[NH2:1][C@H:2]1[CH2:8][CH2:7][C@@H:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]=[N+:17]=[N-:18])[CH2:5][N:4]([CH3:19])[C:3]1=[O:20].[CH3:21][C:22]([CH3:40])([CH3:39])/[CH:23]=[CH:24]/[C@H:25]1[O:30][C:29]([CH3:32])([CH3:31])[O:28][CH:27]2[CH:33]([O:37][CH3:38])[C:34](=[O:36])[O:35][C@H:26]12>C(O)(C)C>[N:16]([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][O:9][C@H:6]1[CH2:5][N:4]([CH3:19])[C:3](=[O:20])[C@@H:2]([NH:1][C:34](=[O:36])[C@@H:33]([C@H:27]2[C@H:26]([OH:35])[C@@H:25](/[CH:24]=[CH:23]/[C:22]([CH3:39])([CH3:21])[CH3:40])[O:30][C:29]([CH3:32])([CH3:31])[O:28]2)[O:37][CH3:38])[CH2:8][CH2:7]1)=[N+:17]=[N-:18]

Participants

4

Reactant 2

HCID 69267460(4R,4aR)-((E)-3,3-dimethyl-but-1-enyl)-7-methoxy-2,2-dimethyl-tetrahydro-furo[3,2-d][1,3]dioxin-6-oneHCID 86609578(3S,6R)-3-amino-6-(6-azido-hexyloxy)-1-methyl-azepan-2-one

Product 1

HCID 86609580(R)-N-[(3S,6R)-6-(6-azido-hexyloxy)-1-methyl-2-oxo-azepan-3-yl]-2-[(4R,5R,6R)-6-((E)-3,3-dimethyl-but-1-enyl)-5-hydroxy-2,2-dimethyl-[1,3]dioxan-4-yl]-2-methoxy-acetamideYield 59.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of (3S,6R)-3-amino-6-(6-azido-hexyloxy)-1-methyl-azepan-2-one (0.207 g, 0.73 mmol) in isopropanol (1 mL) is added (4R,4aR)-((E)-3,3-dimethyl-but-1-enyl)-7-methoxy-2,2-dimethyl-tetrahydro-furo[3,2-d][1,3]dioxin-6-one (0.3 g, 1 mmol) and heated to reflux for 18 h. The solution is evaporated under vacuum adsorbed on silica and chromatographed (CH2Cl2 to EtOAc gradient) to give 0.245 g (59%) of (R)-N-[(3S,6R)-6-(6-azido-hexyloxy)-1-methyl-2-oxo-azepan-3-yl]-2-[(4R,5R,6R)-6-((E)-3,3-dimethyl-but-1-enyl)-5-hydroxy-2,2-dimethyl-[1,3]dioxan-4-yl]-2-methoxy-acetamide as a solid. (ESI) 568.1 (M+H)+

Workup

  1. temperatureheated
  2. temperatureto reflux for 18 h
  3. customThe solution is evaporated under vacuum
  4. customchromatographed (CH2Cl2 to EtOAc gradient)

Sources & evidence

ORD record
ord-6165aeba51384290803a3582d81449c6
Source dataset
uspto-grants-2008_05
Patent number
US07378410B2

Reaction notes

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