Diisopropylethylamine → Pent-4-enyl (2R,4R,6R)-2-Methoxy-2-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-6-(pent-4-enyl)-tetrahydro-2H-pyran-4-ylcarbamate

HRID 1445404Notes

Reaction equation

HRID 1445404 reaction equation
[NH2:1][C@@H:2]1[CH2:7][C@@H:6]([CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12])[O:5][C@:4]([C@@H:15]2[CH2:19][S:18][C:17](=[O:20])[N:16]2[CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)([O:13][CH3:14])[CH2:3]1.[C:30](=O)([O:41]CCCC=C)[O:31][C:32]1C=[CH:36][C:35]([N+]([O-])=O)=[CH:34][CH:33]=1.C(N(C(C)C)CC)(C)C>ClCCl.CN(C1C=CN=CC=1)C>[CH3:14][O:13][C@:4]1([C@@H:15]2[CH2:19][S:18][C:17](=[O:20])[N:16]2[CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[CH2:3][C@H:2]([NH:1][C:30](=[O:41])[O:31][CH2:32][CH2:33][CH2:34][CH:35]=[CH2:36])[CH2:7][C@@H:6]([CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12])[O:5]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 59644046(R)-4-((2R,4R,6R)-4-Amino-2-methoxy-6-(pent-4-enyl)-tetrahydro-2H-pyran-2-yl)-3-(4-methoxybenzyl)thiazolidin-2-oneHCID 674411104-Nitrophenyl pent-4-enyl carbonate

Product 1

HCID 59644051Pent-4-enyl (2R,4R,6R)-2-Methoxy-2-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-6-(pent-4-enyl)-tetrahydro-2H-pyran-4-ylcarbamateYield 83%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of the title compound from Example 67 (113 mg, 0.269 mmol) in dichloromethane (2 mL) was treated with a solution of 4-nitrophenyl pent-4-enyl carbonate (88 mg, 0.35 mmol) in dichloromethane (0.8 mL), diisopropylethylamine (0.061 mL, 0.35 mmol), and a catalytic amount of DMAP (0.2 mg). The mixture was stirred for 24 h, after which it was chromatographed directly on silica gel, eluting with ethyl acetate/dichloromethane, to give the title compound (119 mg, 83%) as an oil.

Workup

  1. customafter which it was chromatographed directly on silica gel
  2. washeluting with ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-c2a0b1f264e14effb485dd325d6e454b
Source dataset
uspto-grants-2010_02
Patent number
US07666861B2

Reaction notes

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