Ethyl bromoacetate → HCID 59997210, compound

HRID 1815578Notes

Reaction equation

HRID 1815578 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([S:10]([N:13]([CH2:38][CH:39]([CH3:41])[CH3:40])[CH2:14][C@@H:15]([OH:37])[C@@H:16]([NH:25][C:26](=[O:36])[O:27][C@@H:28]3[C@H:35]4[C@H:31]([O:32][CH2:33][CH2:34]4)[O:30][CH2:29]3)[CH2:17][C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)(=[O:12])=[O:11])=[CH:9][C:4]=2[O:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:49][C:50]([O:52][CH2:53][CH3:54])=[O:51]>CN(C)C=O.C(OCC)(=O)C>[O:30]1[C@H:31]2[O:32][CH2:33][CH2:34][C@H:35]2[C@@H:28]([O:27][C:26]([NH:25][C@H:16]([C@H:15]([OH:37])[CH2:14][N:13]([S:10]([C:8]2[CH:7]=[CH:6][C:5]3[O:1][CH2:2][O:3][C:4]=3[CH:9]=2)(=[O:12])=[O:11])[CH2:38][CH:39]([CH3:41])[CH3:40])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:49][C:50]([O:52][CH2:53][CH3:54])=[O:51])=[CH:20][CH:19]=2)=[O:36])[CH2:29]1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 59997191(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl) (isobutyl)amino]-2-hydroxy-1-(4-hydroxybenzyl)propylcarbamate

Product 1

HCID 59997210HCID 59997210, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred mixture of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-2-hydroxy-1-(4-hydroxybenzyl)propylcarbamate (200 mg, 0.34 mmol) and cesium carbonate (330 mg, 1.0 mmol) in N,N-dimethylformamide (5 mL) was added ethyl bromoacetate (75 μL, 0.67 mmol). After stirring at ambient temperature for 2 h, the reaction was diluted with ethyl acetate (50 mL), washed with water (3×40 mL), dried (magnesium sulfate) and concentrated in vacuo. The residue was purified by silica gel chromatography (60:40; ethyl acetate:hexane) to afford the title compound (162 mg, 71%) as a white foam. 1H NMR (DMSO-d6): δ 0.78 (6H, dd), 1.16 (3H, t), 1.17-1.43 (2H, m), 1.92 (1H, m), 2.35 (1H, t), 2.64-2.78 (3H, m), 2.88-3.01 (2H, m), 3.24-3.29 (1H, m), 3.40-3.60 (4H, m), 3.70 (1H, t), 3.78-3.82 (1H, m), 4.10 (2H, q), 4.65 (2H, s), 4.81 (1H, q), 5.00 (1H, d), 5.46 (1H, d), 6.12 (2H, s), 6.73 (2H, d), 7.02-7.07 (3H, m), 7.20-7.28 (3H, m); MS: 679 (MH+)

Workup

  1. washwashed with water (3×40 mL)
  2. dry with materialdried (magnesium sulfate)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel chromatography (60:40; ethyl acetate:hexane)

Sources & evidence

ORD record
ord-a6193796a0114e80866e5162aa5adc5c
Source dataset
uspto-grants-2005_04
Patent number
US06878728B1

Reaction notes

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