Dicyclohexylcarbodiimide → 3-Benzyloxypropyl 9-(1,3-benzodioxol-5-yl)-8-(benzyloxymethyl)benzo[g][1,3]benzodioxole-7-carboxylate

HRID 2354593Notes

Reaction equation

HRID 2354593 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:11]([CH2:26][O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[C:12]([C:23]([OH:25])=[O:24])[CH:13]=[C:14]4[C:22]=3[C:18]3[O:19][CH2:20][O:21][C:17]=3[CH:16]=[CH:15]4)=[CH:9][C:4]=2[O:3][CH2:2]1.[CH2:35]([O:42][CH2:43][CH2:44][CH2:45]O)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:35]([O:42][CH2:43][CH2:44][CH2:45][O:24][C:23]([C:12]1[CH:13]=[C:14]2[C:22](=[C:10]([C:8]3[CH:7]=[CH:6][C:5]4[O:1][CH2:2][O:3][C:4]=4[CH:9]=3)[C:11]=1[CH2:26][O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:18]1[O:19][CH2:20][O:21][C:17]=1[CH:16]=[CH:15]2)=[O:25])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 3479713-Benzyloxy-1-propanolHCID 52737799-(1,3-Benzodioxol-5-yl)-8-(benzyloxymethyl)benzo[g][1,3]benzodioxole-7-carboxylic acid

Product 1

HCID 52737803-Benzyloxypropyl 9-(1,3-benzodioxol-5-yl)-8-(benzyloxymethyl)benzo[g][1,3]benzodioxole-7-carboxylateYield 101.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Compound 5 (54.8 mg, 0.12 mmol) in CH2Cl2 (2 mL) at 0° C. was added dropwise to a stirred solution of 3-benzyloxy-1-propanol (16.6 mg, 0.1 mmol), 1,3-dicyclohexylcarbodiimide (31 mg, 0.15 mmol) and 4-dimethylaminopyridine (14.6 mg, 0.12 mmol) in dry CH2Cl2 (1 mL). The mixture was stirred for 4 h at room temperature and concentrated in vacuo. The residue was chromatographed over silica gel using CH2Cl2/MeOH (50:1, v/v) to give 6 (61.2 mg, 84%) as a yellow liquid. 1H NMR (CDCl3) δ 8.16 (s, 1H, H4), 7.47 (d, 1H, H5, J=8.7 Hz), 7.20-7.45 (m, 11H, H6+2×OCH2Ph), 6.82 (d, 1H, H5′, J=7.8 Hz), 6.76 (d, 1H, H2′, J=1.5 Hz), 6.70 (dd, 1H, H6′, J=1.5, 7.8 Hz), 6.06 (AB, 2H, 3′,4′-OCH2O—, Δδ=9.9 Hz, J=1.5 Hz), 5.84 (AB, 2H, 7,8-OCH2O—, Δδ=4.5 Hz, J=1.5 Hz), 4.65 (s, 2H, OCH2Ph), 4.53 (s, 2H, OCH2Ph), 4.42 (t, 2H, 3-COOCH2(CH2)2OBn, J=6.3 Hz), 4.35 (s, 2H, 2-CH2OBn), 3.62 (t, 2H, 3-COO(CH2)2CH2OBn, J=6.3 Hz), 2.06 (quintet, 2H, 3-COOCH2CH2CH2OBn, J=6.3 Hz); MS (EI) m/z 604 [M]+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-ae887169e7484087849d813513d4322e
Source dataset
uspto-grants-2010_07
Patent number
US07754718B2

Reaction notes

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